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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Mike Bannon | 107 | 2003-2014 | |
| 2 | Frank Edwards | 104 | 2010-2022 | |
| 3 | Steve Hayes | 93 | 2014-2022 | |
| 4 | António González | 90 | 2007-2021 | |
| 5 | Tim Redding | 85 | 2001-2016 | |
| 5 | Mike Wood | 85 | 2005-2014 | |
| 7 | Jason Johnson | 83 | 1997-2008 | |
| 7 | Kyle Lohse | 83 | 2001-2014 | |
| 9 | Mario Cruz | 82 | 2016-2027 | |
| 10 | Shawn Sedlacek | 81 | 2002-2014 | |
| 11 | Jerome Williams | 80 | 2003-2016 | |
| 12 | Cody Wade | 79 | 2009-2019 | |
| 13 | Denny Bautista | 77 | 2005-2015 | |
| 13 | Eric Brennan# | 77 | 2023-2031 | |
| 13 | Byron Guffin | 77 | 2010-2022 | |
| 16 | Chuck Smith | 76 | 2008-2016 | |
| 17 | José Tañón | 75 | 2001-2011 | |
| 18 | Phil Barnes | 74 | 2009-2020 | |
| 18 | Rob Dixon | 74 | 2002-2016 | |
| 18 | Sean Lee | 74 | 2012-2022 | |
| 21 | Jason Dickson | 73 | 1996-2006 | |
| 21 | Leonardo Rodríguez | 73 | 2001-2013 | |
| 23 | Armando Galarraga | 72 | 2009-2021 | |
| 24 | Eduardo Ruíz | 69 | 2015-2025 | |
| 25 | Blake Thompson | 68 | 2003-2009 | |
| 26 | Gilbert Carson | 67 | 2008-2021 | |
| 26 | Lee Rice | 67 | 2000-2009 | |
| 28 | Dave Adams# | 66 | 2022-2031 | |
| 28 | Nick Bradley | 66 | 2005-2011 | |
| 28 | Enrique Guerrero | 66 | 2006-2012 | |
| 28 | Steven Holroyd | 66 | 2013-2027 | |
| 28 | Willie Parker | 66 | 2003-2015 | |
| 28 | Luke Prokopec | 66 | 2000-2013 | |
| 34 | Haywood Horn | 65 | 2003-2015 | |
| 35 | Veríssimo Hervedeiro | 64 | 2004-2015 | |
| 36 | Terry Duffy | 63 | 2009-2020 | |
| 37 | Dan Ainslie | 62 | 2016-2027 | |
| 37 | Dave Allen | 62 | 2001-2009 | |
| 37 | Dan C Smith | 62 | 1999-2005 | |
| 40 | Kyle Dawson | 60 | 2010-2017 | |
| 41 | Doug Ball | 59 | 2007-2021 | |
| 41 | Todd Coffey | 59 | 2008-2018 | |
| 41 | P.J. Fortier | 59 | 2003-2012 | |
| 41 | Esteban Martínez | 59 | 2000-2011 | |
| 41 | Daisuke Matsuzaka | 59 | 2010-2023 | |
| 41 | Andrés Silva | 59 | 2014-2025 | |
| 47 | Joaquin Benoit | 58 | 2001-2012 | |
| 47 | John Lannan | 58 | 2011-2020 | |
| 47 | Brandon Lyon | 58 | 2001-2011 | |
| 47 | Dan Middleton | 58 | 2008-2018 | |
| 47 | David Rodríguez | 58 | 2000-2009 | |
| 47 | Jason Williams | 58 | 2014-2024 | |
| 53 | Floyd Johnston | 57 | 2005-2012 | |
| 53 | Luis Marino | 57 | 2005-2012 | |
| 55 | Ned Ames | 56 | 2012-2023 | |
| 55 | Kevin Chamberlain | 56 | 2002-2011 | |
| 55 | James Miller | 56 | 2016-2024 | |
| 55 | Steven Miller | 56 | 2018-2029 | |
| 55 | Paul Williams | 56 | 2012-2026 | |
| 60 | Denis Boucher | 55 | 1992-2003 | |
| 60 | George Burke# | 55 | 2017-2031 | |
| 60 | David Bush | 55 | 2005-2017 | |
| 60 | Damon Lane | 55 | 2010-2018 | |
| 60 | Theron Prince | 55 | 2000-2012 | |
| 60 | Ryan Rupe | 55 | 2002-2009 | |
| 66 | Chris C George | 54 | 2001-2014 | |
| 66 | Glenn Grady | 54 | 2012-2021 | |
| 66 | Roger Powell | 54 | 2020-2031 | |
| 66 | Alan Reynolds | 54 | 2000-2013 | |
| 66 | James Shields | 54 | 2008-2019 | |
| 71 | Curt Cameron | 53 | 2000-2011 | |
| 71 | Bob Harper | 53 | 2011-2024 | |
| 71 | Jim Parque | 53 | 1998-2010 | |
| 71 | Juan Rivera | 53 | 2002-2010 | |
| 71 | Markus Schmidt | 53 | 2003-2013 | |
| 71 | Larry Sherman | 53 | 2002-2010 | |
| 71 | Pablo Torres | 53 | 2000-2009 | |
| 71 | George Yates | 53 | 2016-2024 | |
| 71 | Raúl Zamora# | 53 | 2025-2031 | |
| 80 | Waldo Brenton | 52 | 2000-2010 | |
| 80 | Ken Cowley# | 52 | 2027-2031 | |
| 80 | Wayne McDaniel | 52 | 2009-2018 | |
| 80 | Ricky Nolasco | 52 | 2007-2015 | |
| 80 | Mitch Ward | 52 | 2009-2019 | |
| 85 | Derek Duffy | 51 | 2002-2013 | |
| 85 | Matt Garza | 51 | 2008-2018 | |
| 85 | Alfredo Guerrero | 51 | 2003-2012 | |
| 85 | Tony McKnight | 51 | 2000-2009 | |
| 85 | Kevin Robinson | 51 | 2009-2022 | |
| 85 | Roger Salkeld | 51 | 1993-2006 | |
| 85 | Julio Teheran | 51 | 2012-2021 | |
| 85 | Salomon Torres | 51 | 1993-2002 | |
| 93 | Bob Anderson | 50 | 2009-2020 | |
| 93 | Rob Brown | 50 | 2008-2014 | |
| 93 | John Lackey | 50 | 2002-2011 | |
| 93 | Curt Stevenson | 50 | 2009-2015 | |
| 93 | Jarrod Washburn | 50 | 1998-2008 | |
| 98 | Filiberto Bolzoni | 49 | 2002-2007 | |
| 98 | Nate Cornejo | 49 | 2002-2011 | |
| 98 | Héctor García | 49 | 2002-2011 |
