| Name | Teams | Seasons | W | L | T | Win% | Pts% | Make Playoffs% | Playoff W | Playoff L | Playoff T | Playoff Win% | Best Record | Titles | Runner-up | MLB Players | MLB% |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Scott Pickler Active | Yarmouth-Dennis (1998–) | 28 | 648 | 513 | 52 | 0.534 | 0.556 | 0.750 | 58 | 40 | 0 | 0.592 | 8 | 6 | 3 | 139 | 12.5% |
| Steve Englert Active | Harwich (2003–) | 23 | 475 | 482 | 35 | 0.479 | 0.496 | 0.652 | 33 | 26 | 0 | 0.559 | 0 | 4 | 1 | 125 | 13.9% |
| Kelly Nicholson Active | Orleans (2005–) | 21 | 467 | 404 | 32 | 0.517 | 0.535 | 0.762 | 24 | 35 | 0 | 0.407 | 5 | 1 | 2 | 125 | 16.4% |
| Jamie Shevchik Active | Brewster (2015–) | 11 | 208 | 224 | 32 | 0.448 | 0.483 | 0.727 | 18 | 15 | 0 | 0.545 | 0 | 2 | 1 | 44 | 8.3% |
| Scott Landers Active | Bourne (2022–) | 5 | 105 | 87 | 16 | 0.505 | 0.543 | 1.000 | 27 | 10 | 0 | 0.730 | 1 | 3 | 2 | 5 | 2.0% |
| Ryan Smyth Active | Wareham (2023–) | 4 | 71 | 90 | 3 | 0.433 | 0.442 | 0.500 | 0 | 3 | 0 | 0.000 | 0 | 0 | 0 | 1 | 0.5% |
| Mitch Karraker Active | Hyannis (2024–) | 3 | 61 | 53 | 6 | 0.508 | 0.533 | 1.000 | 3 | 5 | 0 | 0.375 | 0 | 0 | 0 | 0 | 0.0% |
| Dennis Cook Active | Chatham (2025–) | 2 | 36 | 38 | 6 | 0.450 | 0.487 | 0.500 | 1 | 2 | 0 | 0.333 | 0 | 0 | 0 | 0 | 0.0% |
| Jack Dahm Active | Falmouth (2026–) | 1 | 17 | 21 | 2 | 0.425 | 0.450 | 1.000 | 0 | 2 | 0 | 0.000 | 0 | 0 | 0 | 0 | 0.0% |
| Rob Cooper Active | Cotuit (2026–) | 1 | 13 | 25 | 2 | 0.325 | 0.350 | 1.000 | 0 | 2 | 0 | 0.000 | 0 | 0 | 0 | 0 | 0.0% |