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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Year | Champion | LgERA | LgAvg | Lg |
|---|---|---|---|---|
| 2015 | Minnesota (DSL) Twins | 4.79 | .252 | DSL |
| 2016 | Houston (DSL) Astros 2 | 4.87 | .250 | DSL |
| 2017 | Texas (DSL) Rangers | 4.91 | .245 | DSL |
| 2018 | Chicago A (DSL) White Sox | 4.80 | .243 | DSL |
| 2019 | Chicago A (DSL) White Sox | 4.64 | .232 | DSL |
| 2020 | Seattle (DSL) Mariners | 4.88 | .237 | DSL |
| 2021 | Chicago A (DSL) White Sox | 4.69 | .232 | DSL |
| 2022 | Chicago A (DSL) White Sox | 4.79 | .233 | DSL |
| 2023 | Chicago A (DSL) White Sox | 4.78 | .230 | DSL |
| 2024 | Chicago A (DSL) White Sox | 4.62 | .226 | DSL |
| 2025 | Chicago A (DSL) White Sox | 4.58 | .228 | DSL |
| 2026 | Chicago A (DSL) White Sox | 4.37 | .230 | DSL |
| 2027 | Chicago A (DSL) White Sox | 4.56 | .233 | DSL |
| 2028 | Chicago A (DSL) White Sox | 4.62 | .232 | DSL |
| 2029 | Chicago A (DSL) White Sox | 4.68 | .229 | DSL |
| 2030 | DSL Northeast (KCA2) Royals 2 | 5.01 | .227 | DSL |
| 2031 | DSL Northeast (KCA2) Royals 2 | 5.07 | .222 | DSL |
| 2032 | DSL Northwest (KCA1) Royals 1 | 5.48 | .228 | DSL |
| 2033 | DSL Northeast (KCA2) Royals 2 | 5.47 | .233 | DSL |
| 2034 | DSL Chicago (A) White Sox | 5.60 | .241 | DSL |
| 2035 | DSL Chicago (A) White Sox | 5.55 | .238 | DSL |
