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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | SHO | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Don Raynor | 11 | 2012-2017 | |
| 2 | Brian Morris | 8 | 2020-2023 | |
| 3 | Juan Betancourt | 7 | 2011-2027 | |
| 3 | Bob Gordon | 7 | 1990-1999 | |
| 3 | Fernando López | 7 | 2005-2011 | |
| 3 | Markus McCauley | 7 | 2016-2021 | |
| 3 | Micah Moran | 7 | 2012-2015 | |
| 8 | Ron Hunt | 6 | 2005-2012 | |
| 8 | Alvin Pitts | 6 | 2025-2035 | |
| 10 | Edelberto Espinho | 5 | 2023-2027 | |
| 10 | Bartolo Fernández | 5 | 2018-2023 | |
| 10 | Alejandro Gusmán | 5 | 1998-1999 | |
| 10 | Kevin Melton | 5 | 1990-1996 | |
| 10 | Cedric Milton | 5 | 1992-1998 | |
| 10 | Nate Potter | 5 | 2003-2017 | |
| 10 | Kento Takahashi | 5 | 2052-2063 | |
| 10 | Jorge Trujillo | 5 | 2011-2016 | |
| 10 | Jaak van Grootveld | 5 | 2021-2024 | |
| 19 | Reese Ashley | 4 | 1996-1997 | |
| 19 | Jorge Cabrera | 4 | 2004-2010 | |
| 19 | Donald Carlson | 4 | 2011-2012 | |
| 19 | Stan Carter | 4 | 1995-1999 | |
| 19 | Chris Copeland | 4 | 2006-2008 | |
| 19 | Manuel Deliz | 4 | 2026-2041 | |
| 19 | Felipe Diaz# | 4 | 2077-2080 | |
| 19 | Cisco Durango | 4 | 2010-2016 | |
| 19 | Russ Fowler | 4 | 2024-2025 | |
| 19 | Joseph Grieco | 4 | 2051-2057 | |
| 19 | George Jackson | 4 | 2011-2012 | |
| 19 | Rudy Jennings | 4 | 2000-2001 | |
| 19 | Erik Lane | 4 | 1990-1998 | |
| 19 | Anthony McBride | 4 | 1990-1992 | |
| 19 | Steve Meesters | 4 | 2065-2071 | |
| 19 | Alex Oaxaca# | 4 | 2077-2079 | |
| 19 | Frank Osborne | 4 | 2016-2019 | |
| 19 | Jimmy Oyola# | 4 | 2075-2075 | |
| 19 | D'Artagnan Raspberry | 4 | 2060-2062 | |
| 19 | Iván Rojas | 4 | 2020-2026 | |
| 19 | Gilbert Russo | 4 | 2065-2069 | |
| 19 | Pedro Ruíz | 4 | 2018-2021 | |
| 19 | Toshiharu Sato | 4 | 2058-2061 | |
| 19 | Davey Shannon | 4 | 1991-1996 | |
| 19 | Mart Sparnaay | 4 | 2051-2059 | |
| 19 | Ernesto Vega | 4 | 2061-2063 | |
| 19 | Barry Ward | 4 | 2007-2011 | |
| 19 | Johnny Young | 4 | 2005-2011 | |
| 19 | Francisco Zapata | 4 | 2005-2009 | |
| 48 | Ricardo Aburto | 3 | 2052-2055 | |
| 48 | Germán Aguilar | 3 | 1993-1996 | |
| 48 | Michael Alston | 3 | 2010-2013 | |
| 48 | Jake Banks | 3 | 2006-2007 | |
| 48 | Vincent Bodine | 3 | 2017-2031 | |
| 48 | Lawrence Boulter | 3 | 2018-2031 | |
| 48 | Robin Brooks | 3 | 2010-2012 | |
| 48 | Slider Brooks# | 3 | 2069-2072 | |
| 48 | Victor Cacho# | 3 | 2071-2074 | |
| 48 | Joan Castellanos | 3 | 2053-2060 | |
| 48 | Roberto Cortéz | 3 | 2011-2013 | |
| 48 | Damon Davis | 3 | 2018-2029 | |
| 48 | Dave Delgado | 3 | 2053-2057 | |
| 48 | Carl DeYoung | 3 | 2012-2031 | |
| 48 | Mark Dickey | 3 | 1992-1993 | |
| 48 | Marcos Díaz | 3 | 1990-1994 | |
| 48 | Alex Ewing | 3 | 2010-2011 | |
| 48 | Roger Flemming | 3 | 2062-2062 | |
| 48 | Pat Foster | 3 | 2007-2016 | |
| 48 | Yuniesky Fritze | 3 | 2059-2059 | |
| 48 | Vern Garbie | 3 | 2059-2060 | |
| 48 | Jon Greene | 3 | 2016-2031 | |
| 48 | Adrián Gutiérrez | 3 | 1996-1997 | |
| 48 | Trent Harris | 3 | 1997-2002 | |
| 48 | Martin Henderson | 3 | 1993-1996 | |
| 48 | Steve Jones | 3 | 1990-1991 | |
| 48 | Gus Juarez# | 3 | 2075-2078 | |
| 48 | Tetsukazu Kaneda# | 3 | 2064-2067 | |
| 48 | Chris Knight | 3 | 2007-2013 | |
| 48 | Alberto Ledesma | 3 | 2013-2018 | |
| 48 | Min-han Lee | 3 | 2073-2075 | |
| 48 | Jeff MacDade | 3 | 2019-2036 | |
| 48 | Richie MacIntosh | 3 | 1991-1994 | |
| 48 | Vaughan Martin | 3 | 2026-2027 | |
| 48 | Ramón Martínez | 3 | 2018-2031 | |
| 48 | Ryan Mena# | 3 | 2078-2078 | |
| 48 | Jorge Mendez# | 3 | 2080-2081 | |
| 48 | Jon Moody | 3 | 2011-2012 | |
| 48 | José Mora | 3 | 1991-1993 | |
| 48 | Harold Morris | 3 | 2024-2026 | |
| 48 | Luis Morín | 3 | 2000-2002 | |
| 48 | Larry O'Colgan | 3 | 1990-1994 | |
| 48 | Curt O'Mullen | 3 | 2020-2020 | |
| 48 | Zachariah Ollson | 3 | 2054-2060 | |
| 48 | Darren Pace | 3 | 2011-2012 | |
| 48 | Andre Perkins | 3 | 2021-2026 | |
| 48 | Juan Ramos | 3 | 2007-2014 | |
| 48 | Eric Ramsey | 3 | 2055-2057 | |
| 48 | Javy Regalado# | 3 | 2065-2067 | |
| 48 | Ramón Rivas | 3 | 2003-2015 | |
| 48 | Pedro Salgado | 3 | 2018-2021 | |
| 48 | Shuzo Sasaki | 3 | 1990-1995 | |
| 48 | Salomé Sieuve# | 3 | 2076-2077 |
