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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Kelvin Pichardo | .0000 | 2004 | |
| 1 | Kent Bottenfield | .0000 | 1986 | |
| 1 | Jose Bautista | .0000 | 1983 | |
| 1 | Paul Marak | .0000 | 1985 | |
| 1 | Oscar Azocar | .0000 | 1984 | |
| 1 | Luis Aquino | .0000 | 1982 | |
| 7 | Ryan Thurston | .1429 | 2018 | |
| 8 | Jose Perdomo | .1830 | 2010 | |
| 9 | Jimmy Anderson | .1891 | 1994 | |
| 10 | Merkin Valdez | .1911 | 2002 | |
| 11 | David Dominguez# | .1935 | 2035 | |
| 12 | Joey Maher | .1990 | 2013 | |
| 13 | Bill Zarate# | .1991 | 2030 | |
| 14 | Jeriome Robertson | .2000 | 1996 | |
| 15 | Jakob Hernandez | .2100 | 2020 | |
| 16 | Yoel Hernandez | .2113 | 2000 | |
| 17 | Zach Duke | .2126 | 2002 | |
| 17 | Arlinthon De Dios | .2126 | 2022 | |
| 19 | Jose Silva | .2133 | 1992 | |
| 20 | Prelander Berroa | .2138 | 2018 | |
| 21 | Tim Baumgarten | .2157 | 2030 | |
| 22 | Jared Klein | .2182 | 2025 | |
| 23 | Enrico Jimenez | .2212 | 2010 | |
| 24 | Denny Bautista | .2213 | 2000 | |
| 25 | Angel G. Rodriguez | .2241 | 2018 | |
| 26 | Antonio Alfonseca | .2254 | 1992 | |
| 27 | D.J. Ferguson | .2255 | 2010 | |
| 28 | Blayne Weller | .2258 | 2009 | |
| 29 | Jose Ramirez | .2275 | 2009 | |
| 30 | Eric Dixon | .2299 | 2025 | |
| 31 | Brendan Bell | .2312 | 2022 | |
| 32 | Wilsen Palacios | .2321 | 2010 | |
| 33 | Juan Gutierrez | .2322 | 2025 | |
| 34 | Daniel Alvarez | .2329 | 2016 | |
| 35 | Darwin Cubillan | .2330 | 1994 | |
| 36 | Nate Beard | .2331 | 2032 | |
| 37 | Jaison Vilera | .2332 | 2017 | |
| 38 | Manny Ortega | .2339 | 2023 | |
| 39 | Edisson Gonzalez | .2348 | 2018 | |
| 40 | Kelvim Escobar | .2363 | 1994 | |
| 41 | Yancorix Adrian | .2366 | 2010 | |
| 42 | Andy Melton | .2381 | 2024 | |
| 43 | Oscar Rojas | .2387 | 2018 | |
| 44 | Scott Iddiols# | .2394 | 2031 | |
| 45 | Zach Clark | .2408 | 2006 | |
| 46 | Cameron Green | .2415 | 2023 | |
| 47 | Manuel Aybar | .2447 | 1994 | |
| 47 | Rich Rodriguez Jr. | .2447 | 2028 | |
| 49 | Jarret Martin | .2453 | 2010 | |
| 50 | Mike Durante | .2460 | 2028 | |
| 51 | Daniel Berlind | .2462 | 2007 | |
| 52 | Ramon Ulacio | .2467 | 2011 | |
| 52 | Anthony Castro | .2467 | 2014 | |
| 54 | Angel Cespedes | .2472 | 2009 | |
| 55 | Cedrick Bowers | .2478 | 1996 | |
| 56 | Randy Mitchell | .2488 | 2023 | |
| 57 | Franklin Parra | .2500 | 2020 | |
| 57 | David Oca | .2500 | 2015 | |
| 57 | Chris Hunt | .2500 | 2018 | |
| 57 | Tim Benedict | .2500 | 2024 | |
| 61 | Adrian Salcedo | .2510 | 2009 | |
| 62 | Kyle Davies | .2512 | 2001 | |
| 63 | Joe Watford | .2523 | 2024 | |
| 64 | Chris Marshall | .2537 | 2025 | |
| 65 | Freddy Zuniga# | .2544 | 2033 | |
| 66 | Hildemaro Requena | .2571 | 2016 | |
| 67 | Jhonathan Diaz | .2578 | 2016 | |
| 67 | Tim Flynn | .2578 | 2025 | |
| 69 | Wil Ledezma | .2579 | 1999 | |
| 70 | Pedro Espinola | .2581 | 2022 | |
| 71 | Jairo Asencio | .2585 | 2004 | |
| 72 | Manny Ramirez# | .2587 | 2024 | |
| 73 | Napoleon Cardenas | .2594 | 2030 | |
| 74 | Robby Bardin# | .2599 | 2022 | |
| 75 | Jose Alonzo | .2605 | 2013 | |
| 76 | Sergio Gomez | .2617 | 2012 | |
| 77 | Chance McIver# | .2619 | 2025 | |
| 78 | Kevin Bursey | .2627 | 2024 | |
| 79 | Rayni Guichardo | .2629 | 2009 | |
| 79 | Mike Strowd | .2629 | 2021 | |
| 81 | Juan Borrego | .2641 | 2021 | |
| 82 | Jeff Ferrell | .2648 | 2010 | |
| 83 | Tristan Pollock# | .2651 | 2032 | |
| 84 | Ken McLaughlin# | .2658 | 2024 | |
| 85 | Mike McRay# | .2659 | 2036 | |
| 86 | Ronald Belisario | .2662 | 2001 | |
| 87 | Ronnie Lemay | .2664 | 2025 | |
| 88 | Rosman Garcia | .2684 | 1998 | |
| 88 | Janick Lopez | .2684 | 2020 | |
| 90 | Brian Pirela | .2689 | 2018 | |
| 91 | Hunter Milam | .2700 | 2022 | |
| 92 | Dan Vu# | .2709 | 2029 | |
| 93 | Jim Runion | .2714 | 2030 | |
| 94 | Danny Quinn | .2717 | 2028 | |
| 95 | Robert Manuel | .2723 | 2005 | |
| 96 | Nelvin Correa | .2734 | 2018 | |
| 97 | Winston Abreu | .2751 | 1994 | |
| 98 | Oscar Abrego | .2757 | 2024 | |
| 99 | Mike Schleicher# | .2764 | 2033 | |
| 100 | Esteban Maria | .2775 | 2033 |
