5.) Jon Gruden (2002 to 2008): 57-55 record
Let’s start with the winningest-coach in franchise history and the last guy to lead the Bucs to the postseason. Gruden, of course, had his most successful year in Tampa in 2002, when he led the Buccaneers to victory in Super Bowl XXXVII over the Oakland Raiders. Speaking of Raiders, Gruden is now the head coach of the Las Vegas squad that will welcome the Bucs to the desert this season for a Sunday night showdown.