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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Date | Player | Win Seasons | |
|---|---|---|---|
| 1999 | Jacobo Sequeiros | 21-3, 2.69 ERA, 190.2 IP, 50 BB and 124 K | |
| 2030 | António Rivera | 20-2, 3.54 ERA, 185.2 IP, 38 BB and 134 K | |
| 2038 | Ánibal Vázquez | 20-2, 2.98 ERA, 126.2 IP, 40 BB and 125 K | |
| 2038 | Jordan Utgraadt | 20-7, 4.12 ERA, 225.0 IP, 57 BB and 174 K | |
| 2039 | Nelson Hernández | 20-6, 3.25 ERA, 205.0 IP, 41 BB and 146 K | |
| 2048 | Niko Skerlic | 20-6, 2.96 ERA, 164.0 IP, 65 BB and 146 K | |
| 2054 | Kurt Hanson | 20-4, 3.12 ERA, 190.1 IP, 56 BB and 169 K |
