Hindsight is 20-20, but here’s a look at the 10 least-deserving award winners of the last two decades, and who actually earned the hardware.
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| Dallas Stars vs Winnipeg Jets | |
| Type: Moneyline - Status: OPEN | |
| Dallas Stars | -145 |
| Winnipeg Jets | +125 |
| Winnipeg Jets vs Dallas Stars | |
| Type: Series Winner - Status: OPEN | |
| Winnipeg Jets | +255 |
| Dallas Stars | -310 |
| Toronto Maple Leafs vs Florida Panthers | |
| Type: Total - Status: OPEN | |
| Under - 1P | -110 |
| Over - 1P | -120 |
| Florida Panthers vs Toronto Maple Leafs | |
| Type: Series Winner - Status: OPEN | |
| Florida Panthers | -200 |
| Toronto Maple Leafs | +170 |
| Washington Capitals vs Carolina Hurricanes | |
| Type: Puck Line - Status: OPEN | |
| Washington Capitals - 1P | -190 |
| Carolina Hurricanes - 1P | +145 |
| Washington Capitals vs Carolina Hurricanes | |
| Type: Series Winner - Status: OPEN | |
| Washington Capitals | +1150 |
| Carolina Hurricanes | -3500 |
