Head to Head: Annie vs. Derek
| Manager | Wins |
|---|---|
| Annie | 4 |
| Derek | 3 |
| Season | Week | Winner | Annie's Teams | Derek's Teams | Score |
|---|---|---|---|---|---|
| 2025 | 3 | Annie | Annie’s Cool Team | Eating W’s | 110.02-72.92 |
| 2024 | 13 | Annie | Annie’s Cool Team | Eating W’s | 140.26-106.84 |
| 2024 | 2 | Derek | Annie’s Cool Team | Eating W’s | 126.54-123.92 |
| 2023 | 13 | Derek | WWJJD | Eating W’s | 138.66-122.36 |
| 2023 | 2 | Derek | WWJJD | Eating W’s | 106.3-92.46 |
| 2022 | 15* | Annie | Country Road Take Me Mahomes | Eating W’s | 124.84-121.28 |
| 2022 | 7 | Annie | Country Road Take Me Mahomes | Eating W’s | 119.24-83.8 |
* indicates a playoff game.