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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | SB | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Demi Orimoloye# | 35 | 2020-2020 | |
| 2 | Trayvon Robinson | 31 | 2013-2016 | |
| 3 | Chris Pieters | 30 | 2020-2021 | |
| 4 | Jay Gonzalez | 29 | 2018-2023 | |
| 5 | Roman Collins | 28 | 2016-2021 | |
| 6 | Brewer Hicklen# | 27 | 2021-2022 | |
| 7 | Tony Kemp | 26 | 2017-2018 | |
| 7 | Chris Roller# | 26 | 2024-2025 | |
| 9 | Caleb Durbin# | 25 | 2023-2025 | |
| 9 | Kellen Strahm# | 25 | 2023-2025 | |
| 11 | Donald Lutz | 24 | 2013-2018 | |
| 11 | Yefri Perez | 24 | 2019-2021 | |
| 13 | Terrance Gore | 23 | 2021-2021 | |
| 13 | Rhylan Thomas# | 23 | 2024-2025 | |
| 15 | Garrett Whitley# | 22 | 2021-2025 | |
| 16 | Rafael Ortega# | 21 | 2015-2019 | |
| 16 | Keenyn Walker | 21 | 2013-2016 | |
| 18 | Jorge Barrosa# | 19 | 2025-2025 | |
| 18 | Matthew Etzel# | 19 | 2025-2025 | |
| 20 | Jake Mangum# | 18 | 2022-2022 | |
| 21 | Cody Milligan# | 17 | 2023-2025 | |
| 22 | Tyler McDonough# | 16 | 2023-2025 | |
| 22 | Leody Taveras# | 16 | 2022-2023 | |
| 24 | Drew Heid | 15 | 2013-2017 | |
| 24 | Alejandro Osuna# | 15 | 2025-2025 | |
| 24 | Alan Roden# | 15 | 2023-2025 | |
| 27 | Jimmy Herron# | 14 | 2021-2025 | |
| 27 | Logan Hill | 14 | 2018-2022 | |
| 29 | Luis Gonzalez# | 13 | 2025-2025 | |
| 29 | Nelson Velazquez# | 13 | 2022-2023 | |
| 31 | Carlos Vidal# | 12 | 2021-2023 | |
| 32 | Stone Garrett# | 11 | 2019-2021 | |
| 32 | Mark Payton# | 11 | 2016-2018 | |
| 34 | Johnny Field | 10 | 2018-2021 | |
| 34 | Kyle Gaedele | 10 | 2014-2016 | |
| 34 | Anthony Gose# | 10 | 2017-2017 | |
| 34 | Jake Peter | 10 | 2016-2021 | |
| 34 | Matt Vierling# | 10 | 2022-2023 | |
| 39 | Brooks Baldwin# | 9 | 2024-2025 | |
| 39 | Michael Guldberg# | 9 | 2022-2023 | |
| 41 | Jeremy Hazelbaker | 8 | 2016-2016 | |
| 41 | Gregory Polanco# | 8 | 2013-2023 | |
| 43 | Forrestt Allday | 7 | 2014-2019 | |
| 43 | Barrett Barnes | 7 | 2015-2022 | |
| 43 | Conner Capel# | 7 | 2020-2025 | |
| 43 | Tyler Hill# | 7 | 2024-2025 | |
| 43 | Bryson Smith | 7 | 2013-2016 | |
| 43 | Aneury Tavarez | 7 | 2016-2019 | |
| 43 | Toby Thomas | 7 | 2018-2018 | |
| 43 | Mark Zagunis | 7 | 2020-2020 | |
| 51 | Wilyer Abreu# | 6 | 2023-2023 | |
| 51 | John Andreoli# | 6 | 2021-2025 | |
| 51 | Xavier Avery | 6 | 2013-2019 | |
| 51 | Julio Borbon | 6 | 2016-2017 | |
| 51 | Carlos Cortes# | 6 | 2020-2022 | |
| 51 | Michael Hermosillo# | 6 | 2023-2023 | |
| 51 | Brennon Lund | 6 | 2019-2022 | |
| 51 | Alexander Palma | 6 | 2018-2018 | |
| 51 | Luke Raley# | 6 | 2019-2021 | |
| 60 | Corey Brown | 5 | 2013-2013 | |
| 60 | Yusniel Diaz# | 5 | 2021-2025 | |
| 60 | Jameson Fisher | 5 | 2018-2022 | |
| 60 | Lourdes Gurriel Jr.# | 5 | 2017-2018 | |
| 64 | Khris Davis | 4 | 2013-2013 | |
| 64 | Juan Duran | 4 | 2015-2024 | |
| 64 | Zach Gibbons | 4 | 2019-2019 | |
| 64 | Brandon Guyer | 4 | 2013-2013 | |
| 64 | Kyle Jensen | 4 | 2016-2018 | |
| 64 | Tim Locastro# | 4 | 2025-2025 | |
| 64 | Julio Morban | 4 | 2013-2015 | |
| 64 | Cesar Puello | 4 | 2014-2014 | |
| 64 | Jack Reinheimer | 4 | 2019-2023 | |
| 64 | Moises Sierra | 4 | 2013-2022 | |
| 64 | Ryan Ward# | 4 | 2022-2025 | |
| 75 | Alexander Canario# | 3 | 2024-2025 | |
| 75 | Zac Fish | 3 | 2016-2017 | |
| 75 | T.J. Friedl# | 3 | 2019-2024 | |
| 75 | Anthony Garcia# | 3 | 2016-2025 | |
| 75 | Matt Juengel | 3 | 2018-2018 | |
| 75 | Ty Moore | 3 | 2018-2019 | |
| 75 | Matt Murton | 3 | 2017-2017 | |
| 75 | Tyler Neslony# | 3 | 2018-2025 | |
| 83 | Billy Burns | 2 | 2014-2021 | |
| 83 | Lawrence Butler# | 2 | 2022-2023 | |
| 83 | Andrew Cain | 2 | 2013-2013 | |
| 83 | Anthony Concepcion | 2 | 2018-2021 | |
| 83 | Brennen Davis# | 2 | 2024-2024 | |
| 83 | Allan de San Miguel | 2 | 2016-2018 | |
| 83 | Corey Dickerson | 2 | 2013-2013 | |
| 83 | Drew Gilbert# | 2 | 2024-2025 | |
| 83 | Jacob Gonzalez# | 2 | 2018-2025 | |
| 83 | Daniel Johnson# | 2 | 2022-2024 | |
| 83 | Mike Papi# | 2 | 2018-2022 | |
| 83 | Bijan Rademacher | 2 | 2019-2019 | |
| 83 | J.D. Salmon-Williams | 2 | 2020-2020 | |
| 83 | Joe Sever | 2 | 2018-2019 | |
| 83 | Aaron Shipman | 2 | 2015-2017 | |
| 83 | George Springer# | 2 | 2015-2015 | |
| 83 | Jesse Winker# | 2 | 2015-2015 | |
| 83 | Ethan Workinger# | 2 | 2025-2025 |
