Head to Head: Kenneth vs. Annie
| Manager | Wins |
|---|---|
| Kenneth | 6 |
| Annie | 2 |
| Season | Week | Winner | Kenneth's Teams | Annie's Teams | Score |
|---|---|---|---|---|---|
| 2024 | 14 | Annie | Pepperoni Jabroni | Annie’s Cool Team | 105.46-97.88 |
| 2024 | 3 | Kenneth | Pepperoni Jabroni | Annie’s Cool Team | 115.56-93.66 |
| 2023 | 15* | Kenneth | Pepperoni Jabroni | WWJJD | 99.8-71.66 |
| 2023 | 5 | Kenneth | Pepperoni Jabroni | WWJJD | 124.94-95.96 |
| 2022 | 8 | Annie | Pepperoni Jabroni | Country Road Take Me Mahomes | 130.26-108.98 |
| 2021 | 13 | Kenneth | Areola Grande | Judge Jeudys | 129.52-85.42 |
| 2021 | 4 | Kenneth | Areola Grande | Judge Jeudys | 155.92-79.44 |
| 2020 | 9 | Kenneth | Areola Grande | TakeMeMahomesTonight | 119.64-108.18 |
* indicates a playoff game.