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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Scott Diamond | 45 | 2013-2021 | |
| 1 | Burch Smith | 45 | 2016-2022 | |
| 1 | Mike Wright | 45 | 2015-2024 | |
| 4 | Nathan Eovaldi# | 43 | 2013-2015 | |
| 5 | Lucas Harrell | 41 | 2013-2018 | |
| 5 | Brett Kennedy# | 41 | 2019-2023 | |
| 7 | Felix Doubront | 40 | 2016-2019 | |
| 7 | Luke Weaver# | 40 | 2017-2024 | |
| 9 | Brandon Cumpton | 39 | 2014-2019 | |
| 10 | Eduardo Rodriguez# | 38 | 2014-2018 | |
| 11 | Brent Honeywell Jr.# | 37 | 2018-2020 | |
| 11 | Brad Mills | 37 | 2013-2017 | |
| 13 | Kwang-hyun Kim# | 36 | 2023-2026 | |
| 13 | Brandon Leibrandt# | 36 | 2018-2025 | |
| 13 | Dillon Overton | 36 | 2016-2022 | |
| 16 | Rafael De Paula | 33 | 2017-2021 | |
| 16 | Vladimir Gutierrez# | 33 | 2020-2026 | |
| 16 | Allen Webster | 33 | 2013-2021 | |
| 19 | Aaron Laffey | 32 | 2013-2017 | |
| 19 | Adalberto Mejia | 32 | 2018-2021 | |
| 19 | Clayton Richard | 32 | 2013-2017 | |
| 22 | Kolby Allard# | 31 | 2018-2021 | |
| 22 | Ryan Feierabend | 31 | 2007-2014 | |
| 22 | Brock Stewart# | 31 | 2017-2023 | |
| 25 | Ronel Blanco# | 30 | 2019-2026 | |
| 25 | Paolo Espino# | 30 | 2016-2025 | |
| 25 | David Hernandez | 30 | 2015-2021 | |
| 25 | Humberto Mejia# | 30 | 2022-2025 | |
| 25 | Brooks Raley# | 30 | 2014-2024 | |
| 25 | Collin Wiles# | 30 | 2022-2025 | |
| 31 | Tyler Alexander# | 29 | 2021-2025 | |
| 31 | Osvaldo Bido# | 29 | 2022-2026 | |
| 31 | Simon Castro | 29 | 2013-2020 | |
| 31 | Jose De Leon# | 29 | 2017-2025 | |
| 31 | Ross Detwiler | 29 | 2014-2024 | |
| 31 | Tommy Milone | 29 | 2016-2023 | |
| 31 | Jacob Nix# | 29 | 2019-2025 | |
| 31 | Rob Scahill | 29 | 2013-2019 | |
| 31 | Braden Shipley | 29 | 2017-2024 | |
| 31 | Tsuyoshi Wada | 29 | 2013-2015 | |
| 31 | Mitch White# | 29 | 2019-2023 | |
| 42 | Trevor Cahill | 28 | 2016-2018 | |
| 42 | Dylan File# | 28 | 2020-2025 | |
| 42 | Andrew Heaney# | 28 | 2015-2018 | |
| 42 | August Schlosser | 28 | 2013-2016 | |
| 42 | Jesse Scholtens# | 28 | 2022-2025 | |
| 47 | Chris Martin# | 27 | 2015-2021 | |
| 47 | Rafael Montero# | 27 | 2016-2025 | |
| 47 | Brent Suter# | 27 | 2017-2023 | |
| 47 | Ken Waldichuk# | 27 | 2020-2026 | |
| 51 | Casey Crosby | 26 | 2013-2016 | |
| 51 | Roenis Elias | 26 | 2015-2018 | |
| 51 | John Gast | 26 | 2013-2017 | |
| 51 | Eric Lauer# | 26 | 2018-2025 | |
| 51 | Todd Redmond | 26 | 2015-2019 | |
| 51 | Angel Rondon# | 26 | 2022-2025 | |
| 57 | Foster Griffin# | 25 | 2018-2025 | |
| 57 | Deolis Guerra | 25 | 2013-2022 | |
| 57 | Spencer Howard# | 25 | 2020-2025 | |
| 57 | Janson Junk# | 25 | 2022-2026 | |
| 57 | Kyle McGowin# | 25 | 2019-2025 | |
| 57 | Sean Mooney# | 25 | 2023-2026 | |
| 57 | Kenny Rosenberg# | 25 | 2022-2026 | |
| 64 | Brandon Dickson | 24 | 2010-2012 | |
| 64 | Dana Eveland | 24 | 2013-2017 | |
| 64 | Drew Hutchison# | 24 | 2013-2025 | |
| 64 | Nicholas Kingham | 24 | 2014-2015 | |
| 64 | Trevor Rogers# | 24 | 2020-2025 | |
| 64 | Aaron Wilkerson# | 24 | 2017-2025 | |
| 70 | Tony Barnette | 23 | 2016-2019 | |
| 70 | Brian Flynn | 23 | 2014-2021 | |
| 70 | Blaine Hardy | 23 | 2013-2023 | |
| 70 | Brad Lincoln | 23 | 2013-2016 | |
| 70 | Juan Nicasio | 23 | 2013-2023 | |
| 70 | David Paulino | 23 | 2018-2021 | |
| 70 | Adrian Sampson | 23 | 2015-2023 | |
| 70 | Alfredo Simon | 23 | 2013-2016 | |
| 70 | Josh Tomlin | 23 | 2013-2022 | |
| 79 | Dylan Dodd# | 22 | 2023-2025 | |
| 79 | John Ely | 22 | 2014-2016 | |
| 79 | Zach Hedges | 22 | 2019-2023 | |
| 79 | Jake Latz# | 22 | 2022-2025 | |
| 79 | Jordan Lyles# | 22 | 2014-2018 | |
| 79 | Nick Neidert# | 22 | 2019-2025 | |
| 79 | Nick Nelson# | 22 | 2022-2025 | |
| 79 | Ethan Small# | 22 | 2022-2026 | |
| 79 | Nicholas Tepesch | 22 | 2015-2017 | |
| 88 | Robbie Erlin | 21 | 2021-2025 | |
| 88 | Josh Lindblom | 21 | 2009-2020 | |
| 88 | Wes Parsons | 21 | 2020-2021 | |
| 88 | Shawn Tolleson | 21 | 2013-2018 | |
| 88 | Chris Volstad | 21 | 2013-2021 | |
| 93 | Clayton Beeter# | 20 | 2023-2026 | |
| 93 | Duane Below | 20 | 2013-2016 | |
| 93 | Scott Blewett# | 20 | 2018-2025 | |
| 93 | Oscar De La Cruz | 20 | 2018-2023 | |
| 93 | Odrisamer Despaigne# | 20 | 2017-2019 | |
| 93 | Buck Farmer# | 20 | 2016-2018 | |
| 93 | Gonzalez Germen | 20 | 2014-2017 | |
| 93 | Brooks Hall | 20 | 2015-2023 |
