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| Progressive Winning Pct Leaderboard | |
| This table is a snapshot of the career, single-season, active, and yearly leaders at the end of each season. | |
| * - Indicates Hall of Fame
Bold - Indicates active player |
| Year | Career | WPct | Single-Season | WPct | Active | WPct | Yearly | WPct |
| 2009 | Bobby Grimes | .9200 | Bobby Grimes | .9200 | ||||
| 2010 | Bobby Grimes | .9200 | James Sousa | .8621 | ||||
| 2011 | Bobby Grimes | .9200 | Jesus Rodriguez | .7778 | ||||
| 2012 | Bobby Grimes | .7949 | Bobby Grimes | .9200 | Bobby Grimes | .7949 | Michael Arnett | .8750 |
| 2013 | Bobby Grimes | .8133 | Bobby Grimes | .9200 | Bobby Grimes | .8133 | Bobby Grimes | .8788 |
| 2014 | Bobby Grimes | .8278 | Bobby Grimes | .9200 | Bobby Grimes | .8278 | Bobby Grimes | .9000 |
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