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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Clarence Byrd# | 12 | 2018-2018 | |
| 2 | Enrique López | 11 | 2019-2019 | |
| 3 | Dave Munier# | 10 | 2027-2027 | |
| 4 | Dave Barnaby# | 9 | 2029-2029 | |
| 4 | Clement Bowden# | 9 | 2029-2030 | |
| 4 | Hugh Bowness | 9 | 2023-2023 | |
| 4 | Walton Huntingford | 9 | 2026-2026 | |
| 4 | Ilies Philibert | 9 | 2014-2014 | |
| 4 | Luis Miguel Toledo | 9 | 2018-2018 | |
| 10 | Tim Conway | 8 | 2020-2020 | |
| 10 | Ed Gratton# | 8 | 2030-2031 | |
| 10 | Earl Lee# | 8 | 2027-2028 | |
| 10 | Bob Lortie | 8 | 2012-2012 | |
| 10 | Romuald Martin | 8 | 2026-2026 | |
| 10 | Ricky Miller | 8 | 2020-2020 | |
| 10 | Keith Noble# | 8 | 2029-2030 | |
| 10 | Ed Yuke | 8 | 2012-2012 | |
| 18 | Paul Barrett# | 7 | 2020-2020 | |
| 18 | Mike Cartier# | 7 | 2029-2029 | |
| 18 | Adrien Clément# | 7 | 2012-2012 | |
| 18 | Dave Conboy# | 7 | 2025-2025 | |
| 18 | Brad Cornell | 7 | 2021-2021 | |
| 18 | Edison Dickie | 7 | 2019-2019 | |
| 18 | Jason Keller# | 7 | 2029-2029 | |
| 18 | Bobby Lloyd# | 7 | 2031-2031 | |
| 18 | Ed Manuel | 7 | 2015-2015 | |
| 18 | Gabin Martin# | 7 | 2023-2023 | |
| 18 | Tyler McCormick | 7 | 2030-2030 | |
| 18 | Robert McLaughlin# | 7 | 2018-2018 | |
| 18 | Bill Neville# | 7 | 2027-2027 | |
| 18 | Thomas Nicolle | 7 | 2016-2016 | |
| 18 | Hideyori Ohayashi# | 7 | 2019-2019 | |
| 18 | John Randall | 7 | 2020-2020 | |
| 18 | Luis Antonio Rodríguez# | 7 | 2021-2021 | |
| 18 | Francisco Rolón | 7 | 2021-2021 | |
| 18 | Bob Roy | 7 | 2021-2021 | |
| 18 | Dallas Savage | 7 | 2018-2018 | |
| 18 | Jon Shipway | 7 | 2021-2021 | |
| 18 | Jamal Underwood | 7 | 2019-2019 | |
| 18 | Devin Vokey | 7 | 2026-2026 | |
| 41 | Jean-Loup Bourdon | 6 | 2016-2016 | |
| 41 | Lincoln Brouillette | 6 | 2013-2013 | |
| 41 | Benjamin Campbell# | 6 | 2019-2019 | |
| 41 | Neil Coffin# | 6 | 2030-2031 | |
| 41 | Jean-Pierre Delannoy | 6 | 2025-2025 | |
| 41 | George Fortin# | 6 | 2026-2026 | |
| 41 | Javier Galindo# | 6 | 2022-2022 | |
| 41 | Ward Gillin# | 6 | 2027-2027 | |
| 41 | Brian Henderson | 6 | 2019-2019 | |
| 41 | Rick Hill# | 6 | 2019-2019 | |
| 41 | Jeff Hodge# | 6 | 2025-2025 | |
| 41 | Walker Hoekstra# | 6 | 2029-2029 | |
| 41 | Zack Hogan# | 6 | 2032-2032 | |
| 41 | Robert Howard# | 6 | 2020-2020 | |
| 41 | Jordan Johnstone | 6 | 2012-2012 | |
| 41 | Alexandre Lallement | 6 | 2014-2014 | |
| 41 | Esteban Lugo | 6 | 2018-2018 | |
| 41 | Rick MacLellan# | 6 | 2023-2023 | |
| 41 | Pat McConnell# | 6 | 2025-2025 | |
| 41 | Henry McGaughey | 6 | 2024-2024 | |
| 41 | Ken Morrow | 6 | 2021-2021 | |
| 41 | Hervé Muller# | 6 | 2023-2023 | |
| 41 | Bill Newton | 6 | 2012-2012 | |
| 41 | Tomás Ontiveros | 6 | 2021-2021 | |
| 41 | Luis Rico | 6 | 2019-2019 | |
| 41 | Bryan Roland | 6 | 2025-2025 | |
| 41 | Kyle Shaw | 6 | 2020-2020 | |
| 41 | Chris Stone | 6 | 2018-2018 | |
| 41 | Corey Sullivan | 6 | 2017-2017 | |
| 41 | James Thompson# | 6 | 2021-2021 | |
| 71 | Harmon Anstey# | 5 | 2026-2026 | |
| 71 | Bill Barbier | 5 | 2026-2026 | |
| 71 | Cyprien Bataille# | 5 | 2028-2028 | |
| 71 | John Black# | 5 | 2024-2024 | |
| 71 | Stéphane Blin | 5 | 2013-2013 | |
| 71 | Daniel Bonnin | 5 | 2016-2016 | |
| 71 | John Bush | 5 | 2018-2018 | |
| 71 | Tony Colón | 5 | 2018-2018 | |
| 71 | Teagan Cooper# | 5 | 2031-2031 | |
| 71 | Bernard Coste# | 5 | 2028-2028 | |
| 71 | Greg Day# | 5 | 2029-2029 | |
| 71 | Desmond Delaney# | 5 | 2027-2027 | |
| 71 | Austin Drake# | 5 | 2031-2031 | |
| 71 | Charlie Duncan# | 5 | 2027-2027 | |
| 71 | Arnaud Durand | 5 | 2023-2023 | |
| 71 | Dave Dyke# | 5 | 2031-2031 | |
| 71 | Bruce Easton# | 5 | 2028-2028 | |
| 71 | Emmanuel Even# | 5 | 2026-2026 | |
| 71 | Layne Farmer# | 5 | 2029-2029 | |
| 71 | Claudio García | 5 | 2018-2018 | |
| 71 | Mike Gilbert | 5 | 2019-2019 | |
| 71 | Dave Gillingham | 5 | 2025-2025 | |
| 71 | Pierre-Jean Guéry | 5 | 2014-2014 | |
| 71 | Norm Hall | 5 | 2028-2028 | |
| 71 | Greg Harrison# | 5 | 2031-2031 | |
| 71 | Steve Hill | 5 | 2022-2022 | |
| 71 | Bill Hoffmann# | 5 | 2028-2028 | |
| 71 | Kennan Johannson | 5 | 2017-2017 | |
| 71 | Steve Keller | 5 | 2018-2018 | |
| 71 | Jayden Kelly# | 5 | 2031-2032 |
