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GAMBLELEDGER

Platform data extraction, W-2G reconciliation, and IRS-compliant session methodology, delivered as CPA-ready reports. AI-enabled. Human-reviewed.

See It In Action

A Real Session Report

Every wager reconciled to a session, every win and loss documented — exactly how a CPA needs to see it.

Session Report — 2025
Gambling activity across platforms · Jan–Feb 2025
Total Wagers
$647.00
Total Payout
$357.75
Winning Sessions
$207.70
Session Losses
($497.25)
Date & TimeYearPlatformBet ID Event NameGame TypeBet Type WagerPayoutWin/Loss ResultWin SessionLoss Session
01-01-2025 09:042025 DraftKings 7142**** Wisconsin @ LSUSports BetParlay $20.00$7.56 ($12.44)Loss ($12.44)
01-01-2025 09:162025 DraftKings 8365**** Tennessee @ IowaSports BetParlay $60.00$18.73 ($41.27)Loss ($41.27)
01-01-2025 12:042025 BetMGM 5291**** Tennessee @ IowaSports BetParlay $100.00$0.00 ($100.00)Loss ($100.00)
01-01-2025 17:012025 BetMGM 4873**** Texas A&M @ TCUSports BetSingle Bet $50.00$0.00 ($50.00)Loss ($50.00)
01-01-2025 18:212025 DraftKings 9034**** Alabama @ MichiganSports BetSingle Bet $100.00$0.00 ($100.00)Loss ($100.00)
01-01-2025 20:542025 BetMGM 3617**** Texas @ WashingtonSports BetSingle Bet $100.00$190.90 $90.90Win $90.90
02-01-2025 19:012025 DraftKings 6428**** DePaul @ UConnSports BetParlay $20.00$5.85 ($14.15)Loss ($14.15)
02-01-2025 19:092025 BetMGM 2956**** East Carolina @ FAUSports BetParlay $20.00$0.00 ($20.00)Loss ($20.00)
02-01-2025 19:192025 DraftKings 8103**** New Mexico @ Col. St.Sports BetParlay $20.00$136.80 $116.80Win $116.80
This is a sample of the session-level format every GambleLedger report follows — full transaction history, platform-by-platform, reconciled session by session.
Our Expertise

The Most Underserved Problem in Tax Practice

Why gambling tax reporting is one of the most misunderstood areas in tax practice — and what we do about it.

The Most Underserved Problem in U.S. Tax Practice: Gambling Session Reporting
The Most Underserved Problem in U.S. Tax Practice: Gambling Session Reporting
Explore GambleLedger

Built for CPAs, Attorneys, and Their Clients

A specialist back office for the one part of tax season nobody wants to own.

About Us

How GambleLedger started, who's behind it, and what we focus on for CPAs, attorneys, and their clients.

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Our Expertise

The underserved problem in gambling tax reporting — and the answers to the questions every CPA asks us.

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Process & Workflow

From intake form to delivered report — exactly how we handle your platform data, start to finish.

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Services & Pricing

Single-platform reports, multi-platform master reports, firm/bulk plans, and crypto gambling add-ons.

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Case Study

How we rebuilt three years of gambling transaction history after a client received an IRS notice.

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Contact Us

Get in touch about session reconciliation, W-2G matching, or your firm's gambling tax documentation needs.

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Ready to Clean Up Your Client's Gambling Tax Records?

Let's talk about session reconciliation, W-2G matching, or your firm's gambling tax documentation needs. We're built for exactly this.

How We Got Here

Our Story

GambleLedger started from our work as a backend accounting partner — and grew into a specialist back office for gambling tax documentation.

GambleLedger started from our work as a backend accounting partner.

We first built our expertise in crypto accounting, where we worked behind accounting firms and supported them with complex, process-driven work. During that journey, one of our long-standing clients asked us to help with a session gambling report.

We started that work to support the client. But the work was deep and complex. It required us to understand how gambling platforms structure their data, how the IRS session method actually works, how W-2Gs need to reconcile against full transaction histories, and how clean records are prepared for a CPA to review.

That experience opened a new direction for us.

Today, GambleLedger is focused on backend data and reconciliation support for CPAs, tax attorneys, and law firms whose clients have gambling activity. We pull raw transaction data from gambling platforms, apply session-level logic consistent with IRS documentation standards, reconcile every W-2G back into the session log, and deliver reports your CPA can work with.

We are not a tax firm, and we do not provide tax advice. We work as a backend data and reconciliation team, helping gamblers and their CPAs keep the records clean, complete, and audit-ready.

Our Team

The People Behind GambleLedger

Piyush Gupta
Piyush Gupta
Co-founder & CEO
Shubham Agrawal
Shubham Agrawal
Co-founder & COO
Deepak Sharma
Deepak Sharma
Chief Delivery Officer (CDO)
Yogita Lodha
Yogita Lodha
Chief Integration Officer (CIO)
Our Focus

Focused on Gambling Transaction Reporting and Reconciliation

Gambling tax reporting has its own language, process, and complexity. Platform data, session logs, W-2G reconciliation, crypto wagers, multi-state activity, and IRS documentation standards all need to connect properly.

Our goal is to become a focused backend data and reconciliation team for serious gamblers and the CPAs who serve them. We want to keep the process simple for the client and the firm, while handling the complexity carefully in the background.

1Platform Data Extraction
2Session-Level Reconciliation
3W-2G Reconciliation
4IRS-Formatted Reporting
5Multi-Platform Coverage
6Crypto Gambling Reporting
7Prior Year Catch-Up
8CPA & Firm Support
Who We Serve

Built for the Professionals Around the Gambler

CPAs, Tax Attorneys & Enrolled Agents

Your client has a gambling problem — not the kind you are thinking. We handle the data so you can handle the tax.

Law Firms

When gambling activity becomes part of a legal matter, we give you clean, structured records to work from.

Partners & Extended Network

Casinos, gambling coaches, podcasters, content creators, financial advisors — if your audience gambles, they will eventually need clean tax records. You send them to us, we handle the documentation, and they come back to you with one less problem. Simple referral arrangements available for qualifying partners.

What We Know

Our Expertise

Gambling tax reporting is one of the most misunderstood areas in tax practice. Here's the problem we solve, and the questions every CPA asks us.

Our Expertise

The Problem We Solve

Gambling tax reporting in the United States is one of the most misunderstood and underserved areas in tax practice.

The Most Underserved Problem in U.S. Tax Practice: Gambling Session Reporting
The Most Underserved Problem in U.S. Tax Practice: Gambling Session Reporting
The Underserved Problem

Gambling tax reporting in the United States is one of the most misunderstood and underserved areas in tax practice. The IRS requires session-level documentation. Most gamblers file on W-2Gs alone. Most CPAs know the session method exists but don't have the time or back-office infrastructure to execute it properly. And underneath all of it sits the actual pain point: pulling transaction histories from gambling platforms is difficult enough that most people simply avoid it.

The Scale of the Problem

In 2023, over 2.3 million Americans reported gambling income to the IRS. Only 629,854 of them itemized and claimed gambling losses. That gap of over 1.6 million filers represents people who either didn't know they could claim session losses, or couldn't produce the documentation to support them.

Source: irs.gov/statistics
The Problem Every CPA Knows
  • Staff logging into online platforms using client credentials, handling password resets, 2FA codes, geo-restrictions, and locked accounts
  • Many platforms requiring repeated customer support follow-ups just to obtain transaction history, with no self-service export option at all
  • Downloading incomplete CSVs one platform at a time, only to later discover missing months of activity
  • Reconciling sportsbook, casino, and wallet transfers manually across multiple platforms
  • Data arriving raw and inconsistently structured across platforms, bonus amounts mixed into stakes, missing fields, no session logic applied
  • Clients relying only on W-2Gs while potentially losing substantial deductible session losses
  • Internal staff spending hours on low-leverage data collection instead of tax preparation and review
  • High risk of incomplete records, unsupported figures, and audit exposure due to fragmented gambling data
What We Deliver
  • End-to-end platform handling, your firm no longer needs to access portals or chase records
  • Complete transaction-history retrieval, including customer support coordination and missing-data follow-ups
  • Data standardized across platforms, with session-level logic applied consistent with IRS documentation standards
  • Every W-2G reconciled back into the session log
  • Clean, session-level gambling reports delivered within 48 hours of receiving the transaction history, in a CPA-ready format
  • Coverage across sportsbooks, online casinos, DFS apps, wallets, and multi-state gambling activity
  • A dedicated offshore gambling-reporting back office built specifically for accounting and tax firms, giving specialized support without needing an in-house team
  • Significant reduction in staff hours spent on gambling reconciliations and manual cleanup work

No estimates. No guesswork. No incomplete records that put your client at audit risk.

Our Expertise

FAQs

Answers to the questions CPAs, tax attorneys, and their clients ask us most.

1
Is our report acceptable by IRS?

Our reports are prepared using established gambling record-keeping principles and widely followed industry methodologies used by tax professionals handling gambling clients. The reporting format is designed to provide clean, organized, and supportable session-level documentation that CPA firms can review and work with confidently.

2
How do you handle client credentials securely?

Client credentials are used strictly for data retrieval during the active engagement only. Access is handled through secure, encrypted channels, and login information is not retained after the work is completed. We also recommend password resets after delivery as an added security best practice.

3
Can the reports be white-labeled with our firm's branding?

Yes. Reports can be delivered with your firm's branding, including your logo, firm name, and contact details, allowing them to integrate seamlessly into your client delivery process. White-label formatting options are available for CPA firm partners based on their requirements.

4
What if the platform data is incomplete?

We identify and document any missing or unavailable data during the reporting process from the list of all platforms provided to us. Additional records are pursued wherever possible, and if certain information ultimately cannot be recovered, the gap is clearly highlighted so the CPA firm has full visibility while reviewing the report.

5
How fast can reports be turned around during busy season?

Turnaround timelines depend on the completeness of the data, number of platforms involved, and overall complexity of the case. In standard scenarios, reports are typically delivered within 72 hours after the required data has been successfully extracted. Cases involving multiple platforms, missing records, or higher transaction volumes may require additional time for accurate reconciliation and review.

6
Does a casino win/loss statement count as sufficient documentation?

A casino-issued win/loss statement is not considered contemporaneous documentation under IRS Publication 529. It is generated by the casino and does not reflect the session-by-session detail the IRS expects. It can serve as supporting evidence alongside a proper session log, but it cannot stand alone as the primary record. Our reports are structured to meet the session-level standard the IRS looks for.

7
Can you reconstruct records if the client kept no documentation during the year?

Yes. We work backwards from the data available on the gambling platforms — transaction history, game history, win/loss statements, and deposit and withdrawal records. While reconstructed records are not as strong as records kept in real time, they provide a structured and supportable account of activity that is significantly more defensible than W-2G-only reporting or no documentation at all.

8
How do you handle cryptocurrency gambling activity?

Cryptocurrency gambling adds a layer of complexity because it involves two separate taxable events, the conversion or use of crypto as a wager, and the gambling outcome itself. The IRS treats crypto as property, meaning any time crypto is used to place a bet, the transaction may trigger a capital gain or loss depending on the cost basis. We document crypto gambling sessions the same way we document fiat gambling, date, platform, game type, amount wagered in USD equivalent, and net result, and also note the crypto conversion details so you can address the capital gains treatment alongside the gambling income.

9
What platforms do you not cover?

We cover all major licensed US-facing gambling platforms. Unlicensed offshore platforms, certain peer-to-peer poker sites, and platforms that retain no transaction history may be beyond what we can extract. If a platform cannot be accessed or has no retrievable data, we document this clearly in the report so you are aware of the gap.

10
Is the service available for prior tax years?

Yes. We can produce session reports for prior tax years as long as the platform data is still accessible.

How It Works

Process & Workflow

From intake form to delivered report — exactly how we handle your platform data, start to finish.

1

You Complete Your Intake Form

Tell us your name, tax year, which platforms you used, and share your credentials or data exports. Our secure form collects everything needed to begin.

2

We Access Your Platform Data

Our team logs into your platforms and handles 2FA codes, login loops, geo-restrictions, and download limits. For the platforms that require rigorous follow-ups, we handle everything on your behalf. We also overcome issues like geofencing.

3

What We Pull From Each Platform

  • Complete Transaction History
  • Complete Bet History
  • Win/Loss Statements
  • W-2G Documents
  • Withdraw/Deposit Statements
  • Bonus and Promotion History
4

The Work Begins

Data from different platforms have different structures, missing fields, and bonus amounts mixed with stakes. We first standardize everything into a single session-level dataset. Considering all the IRS requirements for each type of activity and all the platform data, the session report is prepared.

5

Your Report Is Delivered Within 72 Hours*

Reports are typically delivered within 72 hours of receiving complete data from all platforms. Turnaround time begins once the required data is available and may vary based on the complexity of the engagement. Learn more in our Services section.

*Turnaround time begins once required data is fully available.
6

How We Handle Your Credentials

  • Access — Credentials are used only for data extraction purposes. Access is not retained after delivery.
  • Storage — All data is handled via encrypted channels. Your raw platform data and passwords are deleted from our systems after your report is confirmed received.
  • Transparency — Every time we log in, we send you the wallet balance before and after our session, so you always know exactly what was there when we accessed your account.
  • Advice — Before we begin, we recommend withdrawing all funds from your platform accounts and avoiding any activity while we extract your data. After delivery, we recommend resetting your platform passwords.
What We Offer

Services & Pricing

From a single platform and single tax year to firm-wide bulk engagements — pick the scope that matches the case in front of you.

Starter
Single Platform
One Gambling Platform · Single Activity · One Tax Year
e.g. DraftKings sports bet only
  • Full data pull from one platform
  • Session-level reconciliation
  • IRS formatted tax report
  • Delivered in 48 hrs
  • One free revision
Get Started
Standard
Single Platform, Multiple Activities
One Gambling Platform · Multiple Activities · One Tax Year
e.g. BetMGM slots + sports bet
  • Full data pull from one platform
  • Session-level reconciliation
  • IRS formatted tax report
  • Delivered in 48 hrs
  • One free revision
Get Started
Firm / Bulk
For CPA Firms, EAs & Referral Partners
 
Built for firms managing multiple clients at once
  • Submit client list, we handle the rest
  • White-label under your firm branding
  • Multiple years + multiple platforms
  • Priority turnaround during tax season
  • Dedicated account manager
Talk to Us
Add-Ons

Extend Any Engagement

Crypto Gambling Add-On

On-chain transaction tracing + session reconciliation for crypto-based gambling.

Prior Year Catch-Up

Session reports for 2–3 prior tax years — ideal for IRS audit prep.

Real Engagement

Case Study

Three years, one IRS notice, and a platform that said the data didn't exist.

How We Rebuilt 3 Years of Gambling Transaction History After an IRS Notice
How We Rebuilt 3 Years of Gambling Transaction History After an IRS Notice (CPA Case Study)
Case Study

Three Years, One Notice, and a Platform That Said the Data Didn't Exist

A CPA partner needed a defensible, session-level accounting of activity going back to 2021 — not just the current tax year — after their client received an IRS notice flagging unreported gambling income.

How It Started

We were brought into this engagement by a CPA partner who had a client in a difficult spot. The client had received an IRS notice flagging unreported gambling income, and the CPA needed a defensible, session level accounting of activity going back to 2021, not just the current tax year. The CPA had the notice and the client relationship. What they didn't have, and what they came to us for, was a way to actually reconstruct three years of betting history from a platform that, on its face, didn't make that possible.

The client himself wasn't a simple case either. He had been active across sports betting, table games, and poker, often within the same stretches of time, all on BetMGM. That mix matters more than it might sound like, because sports bets, casino games, and poker tournaments each follow different session logic under IRS guidance. Before we could even think about totals, we needed to separate three years of mixed activity by type.

The First Wall: A Platform That Only Remembered Six Months

The moment we requested the underlying data, the scope of the problem became clear. BetMGM's self service tools only displayed the trailing six months of account activity. There was no export function. Nothing to click, nothing to download. For a notice that reached back to 2021, that meant roughly two and a half years of exactly the data we needed simply wasn't visible through any normal channel the client or we could access.

This is where a straightforward data request turned into something closer to a sustained negotiation with the platform itself.

Two Weeks of Pushing Against a Moving Target

Getting BetMGM to release historical data outside its standard retention window took nearly two weeks of continuous back and forth, and the friction wasn't a single obstacle. It was several, stacked on top of each other.

Support was chat only. There was no email channel, and nothing in writing carried over from one conversation to the next. Every time we needed to reference something said earlier, there was no record to point back to. We ended up re-explaining the same request more than once simply because of this.

The answers we received depended entirely on who happened to answer. One agent confirmed that data going back to 2021 existed and could be retrieved. The next day, a different agent told us flatly that anything older than six months was no longer available. There was no way to reconcile these two answers, because neither one was ever documented anywhere we could refer back to.

More than once, support tried to close the request out entirely by offering the annual win loss statement instead, and pushed back when we explained that a summary wasn't sufficient. A net win loss figure tells you nothing about individual sessions, doesn't separate sports betting from table games from poker, and wouldn't have given the CPA anything usable to respond to an IRS notice with. We held that line every time it came up.

On top of all this, every login to the account required two factor authentication, with a one time code sent live to the client's phone. Coordinating that in real time, across two weeks of intermittent back and forth with a client who had his own work schedule to manage, added friction to nearly every step along the way.

Eventually, the persistence paid off. BetMGM agreed to pull historical data covering the full 2021 to 2024 window.

The Twist: What Came Back Wasn't What We Asked For

The first file BetMGM sent wasn't a transaction level bet history at all. It was a wallet history, a record of deposits, withdrawals, and account balance movement. Useful for tracking cash flow, but completely useless for reconstructing what was actually wagered, on what, and with what outcome. We went back to support again, specifically clarifying the difference between wallet activity and bet level transaction history, and waited for a corrected file.

When the second file finally arrived, we didn't take it at face value. We cross checked it line by line against the annual statements available directly on the platform, and found gaps. Stretches of activity reflected in the annual summary simply weren't present in the detailed export. That meant a third round of follow up, on top of the two weeks already spent just getting any historical data released in the first place.

What Three Years of Raw Data Actually Looked Like

Once the file was finally complete, the real work began. This wasn't a clean spreadsheet. It was hundreds of thousands of individual bet level rows spanning three years and three different activity types, with no consistent structure to speak of. Tracing session level activity by hand simply wasn't realistic at this volume. The data needed to be systematically normalized before any session logic could be applied at all.

A few of the specific problems we worked through along the way.

Date formats that changed mid file.
Some records used MM/DD/YYYY, others used raw timestamps, and the inconsistency wasn't even limited to different sections of the export. Every date had to be normalized before anything downstream could be trusted.
Time zones that didn't match.
Some records were logged in EST, others in UTC. Left uncorrected, this shifts session boundaries in ways that matter directly. A bet placed at 11:45 PM local time can appear to fall on the wrong calendar day entirely if the time zone isn't corrected first.
Voided bets hiding inside loss totals.
Nothing in the file distinguished a voided bet from a real settled loss. Left as is, this would have inflated the client's reported losses incorrectly across multiple sessions. Each one had to be identified and pulled out individually.
Parlays broken into individual legs.
Rather than appearing as a single wager, each leg of a parlay bet showed up as its own separate row. Left unregrouped, this both inflated the total bet count and distorted session math. A four leg parlay would have looked like four unrelated bets instead of the one wager it actually was.

Bringing It Together

With the data finally clean and normalized, we separated three years of activity by type, sports betting, table games, and poker, and applied session level methodology to each category independently, consistent with how the IRS treats them differently. What started as an unusable wallet history and a platform insisting six months was all that existed eventually became a defensible, session by session reconstruction of the client's full gambling activity from 2021 through 2024.

The Takeaway

For the CPA, this meant something they didn't have at the start of the engagement. An actual position to respond to the IRS notice with, rather than a thin annual summary that raised more questions than it answered. For us, it was a reminder that the hardest part of this work often isn't the tax methodology. It's the two weeks of persistence it takes just to get a platform to acknowledge that the data still exists at all.

Get in Touch

Let's Talk About Your Gambling Tax Documentation

Session reconciliation, W-2G matching, firm/bulk engagements — reach out and we'll get back to you.

Contact Information

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Address

203, 2nd Floor, Sunrise Avenue,
Commerce Six Road, Navrangpura,
Ahmedabad, Gujarat, India 380009

GambleLedger is a data and reporting service, not a CPA firm, tax advisor, or law firm. Reports should be reviewed by a qualified tax professional before filing.