| Year | Team | W | L | T | PO | Points | Result |
|---|---|---|---|---|---|---|---|
| 2015 |  That's What She Said |
5 | 8 | 0 | — | 1,383.26 | |
| 2016 |  Today Was a Good Day |
11 | 2 | 0 | 2-1 | 1,764.70 | |
| 2017 | Today Was a Good Day |
10 | 3 | 0 | 2-1 | 2,105.00 | |
| 2018 | Today Was a Good Day |
8 | 3 | 0 | 3-1 | 2,024.98 | |
| 2019 |  Brady Sits Down to #1 |
10 | 3 | 0 | 1-1 | 1,744.16 | |
| 2020 | Brady Sits Down to #1 |
3 | 8 | 0 | — | 1,363.68 | |
| 2022 | Brady Sits Down to #1 |
8 | 4 | 0 | 0-1 | 1,883.08 | |
| 2023 | Brady Sits Down to #1 |
5 | 6 | 0 | — | 1,653.32 | |
| 2024 | Brady Sits Down to #1 |
7 | 4 | 0 | 0-1 | 1,657.60 | |
| 2025 | Brady Sits Down to #1 |
3 | 11 | 0 | — | 1,789.94 | |
| 2026* (best season) | Brady Sits Down to #1 |
6 | 1 | 0 | — | 1,114.26 |
| Year | Team | W | L | T | PO | Points | Result |
|---|---|---|---|---|---|---|---|
| 2024 |  Baltimore Orioles |
9 | 13 | 0 | — | 5,308.00 | |
| 2025 | Baltimore Orioles |
12 | 10 | 0 | 0-1 | 5,455.00 | |
| 2026* (best season) | Baltimore Orioles |
16 | 6 | 0 | 1-1 | 6,207.00 |
| Year | Team | W | L | T | PO | Points | Result |
|---|---|---|---|---|---|---|---|
| 2026* (best season) |  Crisfield Crabbers |
5 | 2 | 0 | — | 1,063.54 |
| Year | Team | W | L | T | PO | Points | Result |
|---|---|---|---|---|---|---|---|
| 2022 |  Baltimore Blackbirds |
7 | 6 | 0 | 1-1 | 1,335.14 | |
| 2023 | Baltimore Blackbirds |
4 | 9 | 0 | — | 1,166.54 | |
| 2024 | Baltimore Blackbirds |
5 | 8 | 0 | — | 1,003.06 | |
| 2025* (best season) | Baltimore Blackbirds |
8 | 5 | 0 | 1-1 | 1,297.58 |
