Each season, contestants rank the MLB playoff teams by confidence. You score a pick's rank if that team makes the playoffs — highest total wins.
| Season | Winner | Contestants | Spots | |
|---|---|---|---|---|
| 2026 Live | Sean (62) | 6 | 12 | |
| 2025 | Joey (54) | 6 | 12 | |
| 2024 | Andrew (57) | 6 | 12 | |
| 2023 | Joey (48) | 6 | 12 | |
| 2022 | Sean (59) | 5 | 12 | |
| 2021 | Rob (40) | 5 | 10 | |
| 2020 | Rob (123) | 5 | 16 | |
| 2019 ASB swaps | Andrew (33) | 5 | 10 | |
| 2018 ASB swaps | Scott (47) | 5 | 10 | |
| 2017 ASB swaps | Sean (45) | 4 | 10 | |
| 2016 ASB swaps | Sean (48) | 4 | 10 |