The team matched on a 5–11 season in 1988, in which finished winning two of their last three games including an upset of the 1988 AFC East Champion Buffalo Bills, a win that was not only Tampa Bay's high point of the season, but turned out to be hugely impactful on the AFC playoff picture, as Buffalo's loss combined with an overtime win by the Cincinnati Bengals over Washington in the season finale meant that the Bengals clinched the home-field advantage that would have otherwise gone to the Bills; Cincinnati ended up winning a close AFC title game at home against Buffalo and got to Super Bowl XXIII.
The season started with a road win against the improved Green Bay Packers, and game two brought the Super Bowl champion San Francisco 49ers and Joe Montana to Tampa Stadium.
On third down, Montana rolled out and ran untouched into the endzone for a winning TD that left a rare sellout crowd stunned and silent in defeat.
It was an impressive win, but then the Bucs lost to the Detroit Lions in the last minute and entered into an overall five-game losing-streak tailspin.
James Wilder Sr.’s final season was highlighted by a 100-yard receiving game in week 9.