With a win on Sunday against the Dallas Cowboys, who are spiraling out of control worse than Britney Spears after her goods got photographed in that limo, Jon Gruden will become the all time wininigest coach in Buccaneers history. With the putrid history of the Bucs, this doesn’t say much, but I thought it was interesting that he will pass all the Gruden haters favorite person in the world Tony Dungy.
| Wins | Coach | Years | Record |
| 56 | Tony Dungy | 1996-01 | 56-46 |
| 56 | Jon Gruden | 2002- | 56-52 |
| 45 | John McKay | 1976-84 | 45-91-1 |
| 23 | Sam Wyche | 1992-95 | 23-41 |
| 19 | Ray Perkins | 1987-90* | 19-41 |
| 5 | Richard Williamson | 1990-91* | 5-15 |
| 4 | Leeman Bennett | 1985-86 | 4-28 |

