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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 | Dillon Overton | 36 | 2016-2022 | |
| 14 | Brandon Leibrandt# | 34 | 2018-2023 | |
| 15 | Rafael De Paula | 33 | 2017-2021 | |
| 15 | Allen Webster | 33 | 2013-2021 | |
| 17 | Aaron Laffey | 32 | 2013-2017 | |
| 17 | Adalberto Mejia | 32 | 2018-2021 | |
| 17 | Clayton Richard | 32 | 2013-2017 | |
| 20 | Kolby Allard# | 31 | 2018-2021 | |
| 20 | Ryan Feierabend | 31 | 2007-2014 | |
| 20 | Brock Stewart# | 31 | 2017-2023 | |
| 23 | Vladimir Gutierrez# | 30 | 2020-2024 | |
| 23 | David Hernandez | 30 | 2015-2021 | |
| 23 | Brooks Raley# | 30 | 2014-2024 | |
| 26 | Simon Castro | 29 | 2013-2020 | |
| 26 | Ross Detwiler | 29 | 2014-2024 | |
| 26 | Paolo Espino# | 29 | 2016-2024 | |
| 26 | Tommy Milone | 29 | 2016-2023 | |
| 26 | Rob Scahill | 29 | 2013-2019 | |
| 26 | Braden Shipley | 29 | 2017-2024 | |
| 26 | Tsuyoshi Wada | 29 | 2013-2015 | |
| 26 | Mitch White# | 29 | 2019-2023 | |
| 26 | Collin Wiles# | 29 | 2022-2025 | |
| 35 | Trevor Cahill | 28 | 2016-2018 | |
| 35 | Andrew Heaney# | 28 | 2015-2018 | |
| 35 | August Schlosser | 28 | 2013-2016 | |
| 38 | Chris Martin# | 27 | 2015-2021 | |
| 38 | Brent Suter# | 27 | 2017-2023 | |
| 40 | Casey Crosby | 26 | 2013-2016 | |
| 40 | Roenis Elias | 26 | 2015-2018 | |
| 40 | John Gast | 26 | 2013-2017 | |
| 40 | Todd Redmond | 26 | 2015-2019 | |
| 44 | Jose De Leon# | 25 | 2017-2024 | |
| 44 | Deolis Guerra | 25 | 2013-2022 | |
| 46 | Brandon Dickson | 24 | 2010-2012 | |
| 46 | Dana Eveland | 24 | 2013-2017 | |
| 46 | Drew Hutchison# | 24 | 2013-2025 | |
| 46 | Nicholas Kingham | 24 | 2014-2015 | |
| 46 | Rafael Montero# | 24 | 2016-2025 | |
| 51 | Tony Barnette | 23 | 2016-2019 | |
| 51 | Brian Flynn | 23 | 2014-2021 | |
| 51 | Blaine Hardy | 23 | 2013-2023 | |
| 51 | Brad Lincoln | 23 | 2013-2016 | |
| 51 | Humberto Mejia# | 23 | 2022-2025 | |
| 51 | Juan Nicasio | 23 | 2013-2023 | |
| 51 | David Paulino | 23 | 2018-2021 | |
| 51 | Adrian Sampson | 23 | 2015-2023 | |
| 51 | Alfredo Simon | 23 | 2013-2016 | |
| 51 | Josh Tomlin | 23 | 2013-2022 | |
| 61 | John Ely | 22 | 2014-2016 | |
| 61 | Zach Hedges | 22 | 2019-2023 | |
| 61 | Jordan Lyles# | 22 | 2014-2018 | |
| 61 | Jesse Scholtens# | 22 | 2022-2025 | |
| 61 | Nicholas Tepesch | 22 | 2015-2017 | |
| 66 | Tyler Alexander# | 21 | 2021-2025 | |
| 66 | Josh Lindblom | 21 | 2009-2020 | |
| 66 | Jacob Nix# | 21 | 2019-2023 | |
| 66 | Wes Parsons | 21 | 2020-2021 | |
| 66 | Ethan Small# | 21 | 2022-2023 | |
| 66 | Shawn Tolleson | 21 | 2013-2018 | |
| 66 | Chris Volstad | 21 | 2013-2021 | |
| 73 | Duane Below | 20 | 2013-2016 | |
| 73 | Oscar De La Cruz | 20 | 2018-2023 | |
| 73 | Odrisamer Despaigne# | 20 | 2017-2019 | |
| 73 | Buck Farmer# | 20 | 2016-2018 | |
| 73 | Dylan File# | 20 | 2020-2025 | |
| 73 | Gonzalez Germen | 20 | 2014-2017 | |
| 73 | Brooks Hall | 20 | 2015-2023 | |
| 73 | Spencer Howard# | 20 | 2020-2025 | |
| 73 | Erik Johnson | 20 | 2015-2017 | |
| 73 | Rob Kaminsky | 20 | 2020-2022 | |
| 73 | Sam Long# | 20 | 2022-2024 | |
| 73 | Brian Matusz | 20 | 2013-2016 | |
| 73 | Aaron Wilkerson# | 20 | 2017-2025 | |
| 86 | Ryan Buchter | 19 | 2014-2022 | |
| 86 | Rubby de la Rosa# | 19 | 2014-2015 | |
| 86 | Junior Guerra | 19 | 2018-2022 | |
| 86 | Felix Jorge | 19 | 2017-2020 | |
| 86 | Kwang-hyun Kim# | 19 | 2023-2025 | |
| 86 | Brian Moran# | 19 | 2016-2024 | |
| 86 | Andy Oliver | 19 | 2014-2015 | |
| 86 | Bryan Price | 19 | 2014-2016 | |
| 86 | Sergio Santos | 19 | 2013-2017 | |
| 95 | Dylan Dodd# | 18 | 2023-2025 | |
| 95 | Jesse Hahn | 18 | 2020-2023 | |
| 95 | David Hess | 18 | 2019-2022 | |
| 95 | Janson Junk# | 18 | 2022-2024 | |
| 95 | Radhames Liz | 18 | 2014-2018 | |
| 95 | Bobby Poyner | 18 | 2018-2022 |
