Head to Head: Bryan vs. Annie
| Manager | Wins |
|---|---|
| Bryan | 5 |
| Annie | 1 |
| Season | Week | Winner | Bryan's Teams | Annie's Teams | Score |
|---|---|---|---|---|---|
| 2019 | 9 | Bryan | Team Talladega | Drank In My Kupp | 123.2-107.6 |
| 2018 | 15* | Bryan | The Shovel Passers | Drank In My Kupp | 83.46-51.04 |
| 2018 | 9 | Bryan | The Shovel Passers | Drank In My Kupp | 137.6-58.66 |
| 2017 | 8 | Bryan | The Shovel Passers | Drank In My Kupp | 92.68-66.82 |
| 2016 | 10 | Bryan | Reed between the lin | NuthinToItButToDoIt | 98.44-92.84 |
| 2016 | 1 | Annie | Reed between the lin | NuthinToItButToDoIt | 109.46-82 |
* indicates a playoff game.