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| Weekly Winner | |||||
| 1999 | 2000 | 2001 | 2002 | 2003 | |
| Winner | Winner | Winner | Winner | Winner | |
| Week 1 | Godfather | TheShit | Craddle Robber (138) | Shleppy (120) | Ballers (109) |
| Week 2 | Pure Money | TheShit | TheShit & IGWT (121) | Shleppy (127) | Sal's Abortion Clinic (144) |
| Week 3 | Craddle Robber | In God We Trust | Ballers (100) | Buckeye (117) | Big N Tasty (79) |
| Week 4 | Godfather | The B210 | Pure Money (127) | The B210 (121) | The B210 (136) |
| Week 5 | Ballers | Pure Money | Ballers (118) | TheShit (123) | Buckeye (119) |
| Week 6 | Ballers | Pure $ & Abortion | Sals Abortion Clinic (108) | TheShit (108) | Big N Tasty (110) |
| Week 7 | LongBall | TheShit | Buckeye (126) | Buckeye (127) | Godfather (107) |
| Week 8 | Ballers | The B210 | GodFather (108) | Buckeye (119) | The Shit (128) |
| Week 9 | Ballers & Shleppy | Nuts | Sals Abortion Clinic (161) | GodFather (113) | Craddle Robber (115) |
| Week 10 | Godfather | Ego | The B210 (123) | The B210 (151) | GF/IGWT/Buckeye (102) |
| Week 11 | Pure Money | GodFather | In God We Trust (126) | Pure Money (114) | Craddle Robber (128) |
| Week 12 | The Commish | Pure Money | Ballers (110) | Buckeye (142) | Shleppy (143) |
| Week 13 | Nuts | GodFather | The B210 (118) | TheShit (146) | Sal's Abortion Clinic (125) |
| Week 14 | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) |
| Week 15 | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) |
| Week 16 | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) | (PLAYOFFS) |
| Week 17 | The Commish | TheShit | Shleppy (113) | TheShit(125) | Buckeye (109) |