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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Pat Hunt# | 50 | 2017-2029 | |
| 2 | Juan Pérez | 38 | 2017-2023 | |
| 3 | Ken Carter | 34 | 2017-2025 | |
| 4 | Carlos Hernández# | 33 | 2021-2028 | |
| 5 | Lance de Valk# | 31 | 2025-2029 | |
| 5 | César González# | 31 | 2020-2029 | |
| 7 | Ben Logan# | 28 | 2019-2023 | |
| 8 | Shawn Arnold# | 27 | 2017-2020 | |
| 8 | John Ball# | 27 | 2023-2027 | |
| 8 | Luis Castrejón# | 27 | 2024-2029 | |
| 8 | Paco Hernández# | 27 | 2021-2027 | |
| 8 | Aurelio López# | 27 | 2019-2021 | |
| 8 | Leif Mayer# | 27 | 2024-2029 | |
| 14 | Stanley Williams# | 26 | 2017-2020 | |
| 15 | Severiano Duclos# | 25 | 2018-2021 | |
| 16 | John Hamilton# | 24 | 2017-2027 | |
| 16 | Pat Horton | 24 | 2021-2022 | |
| 16 | Jesús López | 24 | 2015-2021 | |
| 16 | Lester Sullivan# | 24 | 2018-2020 | |
| 20 | Jeff Cox | 23 | 2018-2021 | |
| 20 | Mike Foltynewicz# | 23 | 2026-2028 | |
| 20 | Titus Parson# | 23 | 2023-2027 | |
| 23 | Hirokichi Kichida | 22 | 2018-2020 | |
| 23 | Doruk Oyan | 22 | 2020-2022 | |
| 25 | Christian Harris# | 21 | 2025-2029 | |
| 25 | Maxime Janssens# | 21 | 2026-2027 | |
| 25 | Luis Ortíz# | 21 | 2020-2026 | |
| 25 | Joseph Reed | 21 | 2018-2023 | |
| 29 | Darius Baxa# | 20 | 2027-2028 | |
| 29 | Jorge Carrión# | 20 | 2020-2025 | |
| 29 | Tom Gaillard | 20 | 2015-2018 | |
| 29 | Teddy Jones | 20 | 2020-2022 | |
| 29 | Kyle McPherson | 20 | 2018-2023 | |
| 29 | Carlos Méndez# | 20 | 2019-2020 | |
| 29 | Phil Miller# | 20 | 2026-2028 | |
| 36 | Art Adams# | 19 | 2017-2019 | |
| 36 | Benjamin Brouwer | 19 | 2021-2022 | |
| 36 | Dave Seals# | 19 | 2025-2028 | |
| 36 | Vernon Turner# | 19 | 2023-2027 | |
| 36 | António Uribe# | 19 | 2018-2021 | |
| 36 | Loeck Visser# | 19 | 2023-2027 | |
| 42 | Brandeis Göller# | 18 | 2022-2023 | |
| 42 | Mack MacDonald# | 18 | 2026-2028 | |
| 42 | Javier Mena# | 18 | 2026-2027 | |
| 42 | Francisco Mora | 18 | 2018-2020 | |
| 42 | Félix Rodríguez | 18 | 2019-2020 | |
| 42 | Damien Scudder# | 18 | 2024-2026 | |
| 42 | Curt Tate# | 18 | 2023-2024 | |
| 49 | António Bruno# | 17 | 2024-2026 | |
| 49 | Steve Bryan# | 17 | 2016-2024 | |
| 49 | Ralph McKinney# | 17 | 2015-2018 | |
| 49 | Gilberto Ramírez# | 17 | 2022-2028 | |
| 49 | Rob Silva# | 17 | 2025-2026 | |
| 49 | Alex Simmons | 17 | 2020-2021 | |
| 49 | Dave Turner# | 17 | 2024-2026 | |
| 49 | Russ Wood# | 17 | 2017-2018 | |
| 57 | Jack King# | 16 | 2025-2026 | |
| 57 | Ramón Leyva | 16 | 2016-2019 | |
| 57 | José López# | 16 | 2022-2024 | |
| 57 | Eric Newell# | 16 | 2017-2019 | |
| 57 | Steve Sanders | 16 | 2015-2019 | |
| 57 | Anthony Snyder | 16 | 2017-2026 | |
| 57 | Santo Velazco# | 16 | 2028-2029 | |
| 57 | Glenn West | 16 | 2018-2019 | |
| 65 | John Boyle | 15 | 2023-2024 | |
| 65 | Mike Brandner# | 15 | 2028-2029 | |
| 65 | David Cole | 15 | 2020-2021 | |
| 65 | Matt Davenport# | 15 | 2026-2028 | |
| 65 | Luis García | 15 | 2016-2018 | |
| 65 | Martin García | 15 | 2017-2020 | |
| 65 | Michael Logan | 15 | 2020-2026 | |
| 65 | Francisco Martínez | 15 | 2025-2026 | |
| 65 | Homer O'Lannigan | 15 | 2022-2023 | |
| 65 | Cobus Reijnen# | 15 | 2023-2027 | |
| 65 | Héctor Silva# | 15 | 2025-2027 | |
| 65 | Dave Stephenson# | 15 | 2026-2027 | |
| 65 | Artie Taylor | 15 | 2015-2016 | |
| 65 | Júlio Villegas | 15 | 2015-2017 | |
| 79 | Arnie Banks# | 14 | 2024-2028 | |
| 79 | César Galló# | 14 | 2021-2022 | |
| 79 | Anthony Graham | 14 | 2015-2016 | |
| 79 | Jason Hamilton# | 14 | 2019-2021 | |
| 79 | Wes Hamm# | 14 | 2020-2020 | |
| 79 | Andrew Hayes | 14 | 2020-2027 | |
| 79 | Jim Johnstone | 14 | 2017-2022 | |
| 79 | Horatio McAllister# | 14 | 2027-2029 | |
| 79 | Jeff Pearce# | 14 | 2027-2029 | |
| 79 | Paco Peña# | 14 | 2023-2026 | |
| 79 | Jeremy Petty | 14 | 2016-2021 | |
| 79 | Alfredo Ríos# | 14 | 2015-2019 | |
| 79 | Kenny Ryan | 14 | 2015-2025 | |
| 79 | Jurgen Sagebrecht# | 14 | 2023-2024 | |
| 79 | Carlos Sánchez# | 14 | 2018-2019 | |
| 79 | Ricardo Sánchez# | 14 | 2023-2026 | |
| 79 | Frank Simmons | 14 | 2020-2021 | |
| 79 | Gonzalo Velásquez | 14 | 2017-2019 | |
| 97 | Miguel Aguilar# | 13 | 2025-2027 | |
| 97 | Antoine Ayuso# | 13 | 2027-2029 | |
| 97 | Marv Bradford# | 13 | 2025-2025 | |
| 97 | Miguel Canó | 13 | 2015-2019 |
