| . | Outlaws League Manager History |
| . | League Commisioners | Years |
| . | Kent Gray | 1989 - 1990 |
| . | Jerry Winarski | 1991 - 1995 |
| . | David Smith | 1996 - 1998 |
| . | Steve Heller | 1999 |
| . | David Smith | 2000 - 2004 |
| . | Brian LeBeck | 2005 - |
| . | Manager | Years | W | L | Pct | Teams |
Titles | Playoffs |
| . | Bruce Barber | 1993 - 2001 | 693 | 691 | .501 | Crackers, Rockets, Sting | 3 Division Titles | 1 World Series ('01) |
| . | Gary Bringhurst | 2002 | 95 | 67 | .586 | High Rollers |
n/a | n/a |
| . | Joe Burton | 1993 - 1995 | 292 | 194 | .601 | Angels, Sharks |
2 Division Titles | n/a |
| . | Chris Conley | 2001 | 72 | 90 | .444 | Pioneers | n/a | n/a |
| . | John Crone | 1993 - 1999 | 549 | 480 | .534 | Carcass, Wormburners | 3 Division Titles | n/a |
| . | Chris Dail | 1993 - 1999 | 549 | 423 | .565 | Overkill, Sparkys, Wahoos |
3 Division Titles | 1 World Series ('93) |
| . | Terry Douthitt | 2005 | 49 | 49 | .500 | Rockets | n/a | n/a |
| . | Scott Drone-Silvers | 2005 - | 168 | 220 | .433 | Gunslingers | n/a | n/a |
| . | Mike Eliyas | 1993 - 2000, 2006 - | 834 | 774 | .519 | Grizzlies, Orioles, Sluggers | 2 Division Titles | 1 World Series ('99) |
| . | Mike Endries | 1998 - 2000 | 210 | 256 | .452 | Visigoths | n/a | n/a |
| . | Robert Endries | 1995 - 2006 | 921 | 967 | .488 | Wildcats | 2 Division Titles | n/a |
| . | Paul Gerstle | 1999 - | 702 | 700 | .501 | Mudducks |
3 Division Titles | n/a |
| . | Kent Gray | 1993 - 1998 | 527 | 445 | .542 | Thunder |
3 Division Titles | 2 World Series ('97, '98) |
| . | Mike Grimm | 1993 - 1997 | 369 | 369 | .500 | Dodgers | 1 Wildcard | 1 World Series ('95) |
| . | Steve Heller | 1995 - 1999, 2005 | 497 | 474 | .512 | Homers, Trolleys |
2 Division Titles | n/a |
| . | William Hines | 2005 - | 173 | 214 | .447 | Warthogs |
1 Division Title | n/a |
| . | Kim Hoffman | 2005 - | 187 | 201 | .482 | Blue Ox, Oxen |
1 Division Title | n/a |
| . | Bill Hoover | 1993 - 2000, 2006 | 595 | 833 | .417 | Blaze |
2 Wildcards | n/a |
| . | Chris Keleher | 1993 - 1999, 2002 | 628 | 638 | .496 | Daisy Cutters, Giants |
1 Division Title | n/a |
| . | Bill Kline | 2001 - 2004 | 242 | 352 | .407 | Outlaw Reds, Wranglers |
1 Wildcard | n/a |
| . | Brian LeBeck | 2003 - | 327 | 419 | .438 | Capones | 3 Wildcards | 1 World Series ('05) |
| . | Marc Lichtenfeld | 1996 - | 1011 | 870 | .537 | Bombers | 2 Division Titles | n/a |
| . | Lenny Lim | 2000 - 2004 | 459 | 297 | .607 | Storm |
5 Division Titles | n/a |
| . | Larry Little Jr | 2001 - | 540 | 549 | .496 | Moonshiners, Rebels |
3 Wildcards | n/a |
| . | Joe Maestro | 2002 - 2004 | 264 | 168 | .611 | Cardinals |
1 Division Title | 2 World Series ('02, '03) |
| . | Hank Nimitz | 1995 - | 1067 | 973 | .523 | Comets |
7 Division Titles | 1 World Series ('06) |
| . | Bryan Oldfield | 2005 | 30 | 38 | .441 | Blue Sox | n/a | n/a |
| . | Erik Rodriguez | 2005 | 46 | 47 | .495 | Warriors |
n/a | n/a |
| . | Elliot Sandle | 1993 - | 1174 | 1201 | .494 | Knights | 2 Division Titles | 1 World Series ('07) |
| . | Curt Seikert | 1996 - 1997 | 134 | 190 | .414 | Angels |
n/a | n/a |
| . | Phil Sharp | 1999 - 2004 | 548 | 532 | .507 | Angels, Gargoyles | 2 Division Titles | n/a |
| . | Randy Shreiner | 2003 - 2005 | 266 | 164 | .619 | Lightning |
2 Division Titles | 1 World Series ('04) |
| . | Edwin Slifker Jr | 2000 - | 533 | 706 | .430 | Orioles | n/a | n/a |
| . | David Smith | 1995 - | 1076 | 963 | .528 | Chauns, Other Team | 6 Division Titles | 2 World Series ('96, '00) |
| . | Rob Stern | 2006 - | 155 | 169 | .478 | Black Sox | 1 Wildcard | n/a |
| . | Steve Taylor | 1993 - 1996 | 332 | 316 | .512 | Lightning | 1 Division Title | 1 World Series ('94) |
| . | Dan Waldron | 1999 - 2005 | 443 | 569 | .438 | Ehs | 2 Wildcards | n/a |
| . | Daymon Ward | 2007- | 59 | 103 | .364 | Pioneers | n/a | n/a |
| . | Merle Watkins | 1999 | 42 | 116 | .266 | Vikings | n/a | n/a |
| . | Jerry Winarski | 1993 - | 1195 | 1155 | .509 | Avalanche, Scorpions |
3 Division Titles | n/a |