Last Update: 18th May 2025
| Date | Event | Bet Selection | Bet Type | Status | Stake | Return | P/L | Money Line | Win Probability |
|---|---|---|---|---|---|---|---|---|---|
| 18-May-2025 | NHL Playoffs 2025 | Toronto Maple Leafs to beat Florida Panthers by 2 Points | Single | Lost | $250,000 | $0 | $-250.00K | 700 | 12.5% |
| 18-May-2025 | NHL Playoffs 2025 | Toronto Maple Leafs to beat Florida Panthers | Single | Lost | $1,000,000 | $0 | $-1.00M | 113 | 46.9% |
| 06-Jun-2024 | NHL Playoffs 23/24 | Edmonton Oilers to win the playoffs outright against Florida Panthers | Single | Lost | $500,000 | $0 | $-500.00K | 105 | 48.8% |
| 05-Jun-2022 | NHL 2022 | New York Rangers to beat Tampa Bay Lightning | Parlay | Lost | $450,586 | $0 | $-450.59K | 135 | 42.6% |
| 16-May-2022 | NHL 2022 |
New York Rangers to beat Pittsburgh Penguins Calgary Flames to beat Dallas Stars |
Parlay | Won | $308,833 | $2,667,048 | $2.36M |
-122 -217 |
55.0% 68.5% |
| 12-May-2022 | NHL Playoffs 2021/22 | Tampa Bay Lighting to beat Toronto Maple Leafs in a 7-game series | Single | Won | $400,000 | $1,200,000 | $800.00K | 200 | 33.3% |
| Entity Name | On to Win – Bets | Against – Bets | Total P&L | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Bets | W/L | Win % | Stake | Return | P/L | Bets | W/L | Win % | Stake | Return | P/L | ||
| Pittsberg Penguins | - | - | - | - | - | - | 1 | 1/0 | 100.0% | $86.08K | $743.34K | $657.27K | $657.27K |
| Calgary Flames | 1 | 1/0 | 100.0% | $69.05K | $596.31K | $527.26K | - | - | - | - | - | - | $527.26K |
| Dallas Stars | - | - | - | - | - | - | 1 | 1/0 | 100.0% | $69.05K | $596.31K | $527.26K | $527.26K |
| Tampa Bay Lighting | 1 | 1/0 | 100.0% | $400.00K | $1.20M | $800.00K | 1 | 0/1 | 0.0% | $273.61K | $0.00 | $-273.61K | $526.39K |
| New York Rangers | 2 | 1/1 | 50.0% | $359.69K | $743.34K | $383.66K | - | - | - | - | - | - | $383.66K |
| Toronto Maple Leafs | 2 | 0/2 | 0.0% | $1.25M | $0.00 | $-1.25M | 1 | 1/0 | 100.0% | $400.00K | $1.20M | $800.00K | $-450.00K |
| Edmonton Oilers | 1 | 0/1 | 0.0% | $500.00K | $0.00 | $-500.00K | - | - | - | - | - | - | $-500.00K |
| Florida Panthers | - | - | - | - | - | - | 3 | 0/3 | 0.0% | $1.75M | $0.00 | $-1.75M | $-1.75M |
| TOTALS | 7 | 3/4 | 42.9% | $2.58M | $2.54M | $-39.09K | 7 | 3/4 | 42.9% | $2.58M | $2.54M | $-39.09K | $-78.17K |
Note: In cases where Drake bet on the outcome of a multi-entity competition or selection — such as a race, award, or NBA Conference winner — there isn't a single, opposing entity to attribute an 'against' bet to. As a result, the profit and loss from these types of bets won't be reflected in the 'Bet Against' P&L column, and the totals may not align exactly with his overall profit and loss.
| Rank | Date | Event | Bet Selection | Bet Type | Status | Stake | Return | P/L | Money Line | Win Probability |
|---|---|---|---|---|---|---|---|---|---|---|
| 1# | 16-May-2022 | NHL 2022 |
New York Rangers to beat Pittsburgh Penguins Calgary Flames to beat Dallas Stars |
Parlay | Won | $308,833 | $2,667,048 | $2.36M |
-122 -217 |
55.0% 68.5% |
| 2# | 12-May-2022 | NHL Playoffs 2021/22 | Tampa Bay Lighting to beat Toronto Maple Leafs in a 7-game series | Single | Won | $400,000 | $1,200,000 | $800.00K | 200 | 33.3% |
| 3# | 18-May-2025 | NHL Playoffs 2025 | Toronto Maple Leafs to beat Florida Panthers by 2 Points | Single | Lost | $250,000 | $0 | $-250.00K | 700 | 12.5% |
| 4# | 05-Jun-2022 | NHL 2022 | New York Rangers to beat Tampa Bay Lightning | Parlay | Lost | $450,586 | $0 | $-450.59K | 135 | 42.6% |
| 5# | 06-Jun-2024 | NHL Playoffs 23/24 | Edmonton Oilers to win the playoffs outright against Florida Panthers | Single | Lost | $500,000 | $0 | $-500.00K | 105 | 48.8% |
| 6# | 18-May-2025 | NHL Playoffs 2025 | Toronto Maple Leafs to beat Florida Panthers | Single | Lost | $1,000,000 | $0 | $-1.00M | 113 | 46.9% |