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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Matt Beard | 108 | 2000-2013 | |
| 2 | Ryan Hester | 87 | 2001-2011 | |
| 3 | Brian Gann | 85 | 2000-2013 | |
| 4 | Sean Cofield# | 82 | 2011-2020 | |
| 5 | Adam Arnett | 79 | 2000-2009 | |
| 6 | Luis Alcoser# | 78 | 2005-2020 | |
| 7 | Jose Estrada | 77 | 2000-2010 | |
| 8 | Jonathan McMahon | 73 | 2001-2009 | |
| 8 | Justin Messer | 73 | 2000-2012 | |
| 8 | Gabe Vincent# | 73 | 2012-2020 | |
| 11 | Justin Steach | 72 | 2004-2014 | |
| 12 | Josh Adams | 70 | 2000-2014 | |
| 12 | Federico Gonzalez | 70 | 2000-2009 | |
| 12 | Enrique Perez# | 70 | 2009-2017 | |
| 15 | Dan Hagen | 69 | 2002-2013 | |
| 15 | Cameron Outlaw# | 69 | 2015-2020 | |
| 17 | Jeremy Excell | 68 | 2000-2012 | |
| 17 | Edgar Gonzalez | 68 | 2000-2009 | |
| 17 | Jonathan Lung | 68 | 2000-2011 | |
| 17 | Jonathan Parker# | 68 | 2011-2020 | |
| 17 | Ian Starcher | 68 | 2000-2012 | |
| 22 | Jim Patrick | 67 | 2000-2011 | |
| 23 | Andy Jackson | 65 | 2005-2013 | |
| 23 | Fred Muse | 65 | 2000-2012 | |
| 25 | Don Sheffield | 64 | 2000-2011 | |
| 26 | Aaron Harrison | 62 | 2000-2010 | |
| 27 | Cameron Brown | 61 | 2011-2018 | |
| 27 | Dan Cormie | 61 | 2008-2017 | |
| 27 | Santiago Rodas | 61 | 2000-2010 | |
| 27 | Brian Yates | 61 | 2003-2012 | |
| 31 | Andy McCullough | 60 | 2000-2014 | |
| 31 | Ramon Sandoval | 60 | 2000-2009 | |
| 31 | Alan Sweet | 60 | 2000-2009 | |
| 34 | Chris Auger | 59 | 2000-2009 | |
| 34 | Mike Felder | 59 | 2004-2014 | |
| 34 | Markus Mensink | 59 | 2000-2008 | |
| 37 | Matt Garcia | 58 | 2004-2013 | |
| 37 | Brad Goodman# | 58 | 2012-2019 | |
| 39 | Tadanori Kawasaki | 57 | 2005-2014 | |
| 39 | Will Moore | 57 | 2000-2009 | |
| 39 | Tom Schauman | 57 | 2003-2010 | |
| 42 | Miguel Gutierres# | 56 | 2013-2020 | |
| 42 | Jay Russell | 56 | 2000-2009 | |
| 44 | Logan Johns | 55 | 2002-2011 | |
| 44 | Alex Padial | 55 | 2005-2018 | |
| 46 | Jon Caruso | 54 | 2004-2013 | |
| 46 | Jose Flores | 54 | 2001-2012 | |
| 46 | Jorge Lopez | 54 | 2000-2013 | |
| 46 | Nelson Martinez# | 54 | 2011-2020 | |
| 46 | Matt Taub | 54 | 2005-2016 | |
| 51 | Nick Giese | 53 | 2000-2009 | |
| 51 | Mike Henken | 53 | 2001-2011 | |
| 51 | Sean Prevost | 53 | 2005-2014 | |
| 51 | Jesus Quintero | 53 | 2000-2009 | |
| 55 | Michael Flood | 52 | 2009-2013 | |
| 55 | Carlos Martinez | 52 | 2005-2016 | |
| 57 | Daniel Bromley | 51 | 2000-2009 | |
| 57 | Javier Martinez | 51 | 2003-2011 | |
| 57 | Roberto Urias | 51 | 2000-2009 | |
| 60 | Brad Parish | 50 | 2000-2008 | |
| 60 | Chris Pickens | 50 | 2005-2013 | |
| 62 | Rogelio Delgado | 49 | 2005-2012 | |
| 62 | Danny Lopez | 49 | 2000-2011 | |
| 62 | Tony Marcano | 49 | 2000-2014 | |
| 62 | Victor Ortega | 49 | 2000-2008 | |
| 62 | Max Shepherd | 49 | 2012-2016 | |
| 67 | Ian Harned | 48 | 2000-2010 | |
| 67 | Arturo Jimenez | 48 | 2003-2013 | |
| 67 | Kevin Overholser | 48 | 2000-2010 | |
| 67 | Alex Pina | 48 | 2000-2009 | |
| 71 | Chad Barber | 47 | 2004-2015 | |
| 71 | Tyler Byrd | 47 | 2000-2011 | |
| 71 | Paul Guidry | 47 | 2000-2008 | |
| 71 | Nick Kline# | 47 | 2007-2018 | |
| 71 | Matt McPeak | 47 | 2000-2006 | |
| 71 | Paul Reining# | 47 | 2013-2020 | |
| 71 | Dustin Robinson# | 47 | 2015-2020 | |
| 71 | Morgan Thompson | 47 | 2005-2014 | |
| 71 | Greg Vanrenen | 47 | 2000-2011 | |
| 80 | Robert Bell | 46 | 2005-2016 | |
| 80 | Seth Bruno | 46 | 2004-2013 | |
| 80 | Miguel Calamaco | 46 | 2010-2015 | |
| 80 | Steve Eck | 46 | 2005-2013 | |
| 80 | Mike Johnson | 46 | 2010-2015 | |
| 80 | Bill Kilmer | 46 | 2000-2006 | |
| 80 | Dan King | 46 | 2009-2015 | |
| 80 | Gerardo Lozano# | 46 | 2014-2020 | |
| 80 | Greg Schultz | 46 | 2010-2018 | |
| 89 | Justin Brooks# | 45 | 2012-2020 | |
| 89 | Alfonso Colon | 45 | 2000-2009 | |
| 89 | Ricardo Cortez | 45 | 2005-2012 | |
| 89 | Alfredo Garza# | 45 | 2012-2017 | |
| 89 | Bruce Hernandez | 45 | 2000-2008 | |
| 89 | Miguel Isiordia | 45 | 2000-2009 | |
| 89 | Tyler Lewis | 45 | 2000-2006 | |
| 89 | Luis Maldonado# | 45 | 2017-2020 | |
| 89 | Danny Michel | 45 | 2002-2011 | |
| 89 | Evan Mintzer# | 45 | 2013-2020 | |
| 89 | Manny Navarro | 45 | 2001-2013 | |
| 89 | Mario Pellot | 45 | 2000-2011 |
