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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | James Scott | 60 | 2022-2029 | |
| 2 | Jason McKinney | 57 | 2015-2024 | |
| 3 | Fernando González | 45 | 2017-2024 | |
| 4 | Cameron Frye# | 44 | 2024-2034 | |
| 5 | Huai-yu Kan | 43 | 2015-2022 | |
| 6 | Tomiji Saikawa | 39 | 2021-2024 | |
| 6 | Chris Sommer# | 39 | 2028-2034 | |
| 8 | Rodger de Meza | 38 | 2022-2026 | |
| 8 | Júlio Hernández | 38 | 2016-2025 | |
| 10 | Nate Rogers | 37 | 2017-2025 | |
| 10 | Edward Whipp | 37 | 2023-2029 | |
| 12 | Juan Lara | 36 | 2025-2029 | |
| 13 | Raúl Pérez | 35 | 2015-2025 | |
| 14 | Ron Barry | 34 | 2015-2019 | |
| 15 | José Sánchez# | 33 | 2025-2032 | |
| 15 | Aaron Wise | 33 | 2017-2023 | |
| 17 | Roberto Aguirre# | 31 | 2022-2032 | |
| 17 | Bryan Houston | 31 | 2019-2026 | |
| 19 | Artie Chávez | 30 | 2022-2027 | |
| 19 | Edgar Lankford# | 30 | 2025-2030 | |
| 21 | Marv Bradford# | 29 | 2027-2029 | |
| 21 | Ricardo Gómez# | 29 | 2028-2034 | |
| 21 | Francisco Sandoval# | 29 | 2029-2034 | |
| 21 | Jeff Sloan | 29 | 2018-2022 | |
| 25 | Robert Dickinson | 28 | 2015-2027 | |
| 25 | Dalton García | 28 | 2015-2032 | |
| 25 | Robinson Suárez# | 28 | 2025-2030 | |
| 25 | Grant White | 28 | 2022-2028 | |
| 29 | Juan Cruz | 27 | 2021-2029 | |
| 29 | Orsino Lippi | 27 | 2018-2020 | |
| 29 | Rafael Méndez# | 27 | 2029-2033 | |
| 29 | Santiago Mesa | 27 | 2024-2029 | |
| 33 | Juan López# | 26 | 2025-2033 | |
| 33 | Ron O'Slattery | 26 | 2015-2023 | |
| 35 | António Alomar# | 25 | 2028-2034 | |
| 35 | Cisco Andr# | 25 | 2030-2033 | |
| 35 | Júlio Martínez# | 25 | 2025-2030 | |
| 35 | Bartolo Ruíz# | 25 | 2030-2034 | |
| 35 | Bernie Sanders# | 25 | 2025-2027 | |
| 40 | Ben Hopley# | 24 | 2029-2032 | |
| 40 | John McCord | 24 | 2023-2028 | |
| 40 | Manny Pérez | 24 | 2024-2029 | |
| 40 | Juan Reyes | 24 | 2024-2028 | |
| 44 | Enea Dini | 23 | 2026-2029 | |
| 44 | Armando Gonzáles# | 23 | 2023-2030 | |
| 44 | Mike Owens# | 23 | 2027-2029 | |
| 44 | Suezo Sato | 23 | 2015-2020 | |
| 44 | Bastião Shwerin | 23 | 2026-2031 | |
| 44 | Jordan Turpin# | 23 | 2029-2034 | |
| 50 | Casey Bader | 22 | 2022-2024 | |
| 50 | Tom Bowen | 22 | 2016-2019 | |
| 50 | Iwane Chihara# | 22 | 2031-2034 | |
| 50 | Luis Cuero# | 22 | 2025-2034 | |
| 50 | Lorenzo Díaz# | 22 | 2031-2034 | |
| 50 | Cole Johnson | 22 | 2016-2020 | |
| 50 | Ben Logan | 22 | 2024-2031 | |
| 50 | Orlando Martínez | 22 | 2015-2025 | |
| 50 | Stanley Neal | 22 | 2021-2024 | |
| 50 | Tim Nelson | 22 | 2017-2019 | |
| 50 | Alfredo Ríos | 22 | 2022-2027 | |
| 61 | Rio Bavin# | 21 | 2026-2033 | |
| 61 | Jorge Cedeño# | 21 | 2027-2029 | |
| 61 | Eugene Clarkston# | 21 | 2023-2034 | |
| 61 | Luis Gonzáles | 21 | 2017-2024 | |
| 61 | Donald Gregory | 21 | 2021-2032 | |
| 61 | Harry Mander | 21 | 2024-2030 | |
| 61 | Javier Romero# | 21 | 2029-2032 | |
| 61 | Russ Rose | 21 | 2017-2021 | |
| 61 | Ken Shelton# | 21 | 2028-2033 | |
| 61 | Millard Taylor# | 21 | 2027-2029 | |
| 61 | Gordon Wiggins | 21 | 2015-2025 | |
| 72 | Alfonso Álvarez# | 20 | 2023-2028 | |
| 72 | Alejandro Arteaga | 20 | 2022-2026 | |
| 72 | Michael Brown# | 20 | 2024-2031 | |
| 72 | Connor Dale | 20 | 2020-2023 | |
| 72 | Eric Newell | 20 | 2020-2024 | |
| 72 | Piotr Oja# | 20 | 2027-2030 | |
| 72 | Bob Payne# | 20 | 2028-2032 | |
| 72 | Alberto Reyes | 20 | 2025-2030 | |
| 72 | Octávio Ríos# | 20 | 2026-2029 | |
| 72 | Valentín Rivera# | 20 | 2026-2031 | |
| 82 | Lawrence Bignold | 19 | 2016-2026 | |
| 82 | Willie Cameron | 19 | 2023-2025 | |
| 82 | Jorge Cruzan# | 19 | 2031-2033 | |
| 82 | Manuel Delgado | 19 | 2016-2026 | |
| 82 | Hank Downey | 19 | 2017-2022 | |
| 82 | Atila Freska# | 19 | 2031-2034 | |
| 82 | Nésto Gago# | 19 | 2031-2034 | |
| 82 | Raúl Gonzáles# | 19 | 2029-2033 | |
| 82 | Doug Green | 19 | 2024-2034 | |
| 82 | Chris Hayes# | 19 | 2029-2034 | |
| 82 | Barry Jones | 19 | 2015-2029 | |
| 82 | Kenny Kawaguchi# | 19 | 2030-2032 | |
| 82 | Kenny Koehler# | 19 | 2026-2028 | |
| 82 | Miguel Angel Liñares | 19 | 2015-2022 | |
| 82 | José López | 19 | 2026-2028 | |
| 82 | Victor Lustig# | 19 | 2031-2034 | |
| 82 | Robert Neal | 19 | 2021-2027 | |
| 82 | Pang Qin# | 19 | 2030-2033 | |
| 82 | Addie Samson# | 19 | 2021-2023 |
