This season is famous for Sam Wyche, Head Coach of the Bucs, saying "Five dash Two" to reporters during a press conference after game 7 in which he basically told reporters "HA I told you so" even though those 5 wins were close games marked by a great deal of luck for the Bucs. Tampa Bay had won 9 of its previous 12 games, going back to the end of the 1994 season, and many observers felt they had become a sleeper NFC playoff contender. However, the good luck and victory string soon ran out. Following the week seven overtime win over Minnesota, Tampa Bay lost three in a row before beating expansion Jacksonville, only after Jaguars coach Tom Coughlin decided to go for a 2-point conversion when scoring a last minute touchdown. It failed and the Bucs won 17–16, giving them a sweep of that season's new expansion teams, as they had beaten Carolina 17–10 in week 5. Two more losses followed, and the 6–7 Buccaneers had a prime time ESPN Sunday Night Football game against the Green Bay Packers, who were playing without standout Reggie White due to injury. Tampa Bay pulled out an overtime win over the heralded Packers to make their record 7–7 and ensured their streak of 10-loss seasons, dating back to the 1983 season, was finished. The Buccaneers even remained in playoff contention in game 14 for the first time since the strike-shortened 1982 season under Doug Williams.
The Bucs however lost to the Chicago Bears by 21 points at Soldier Field and their playoff hopes were ruined. In the season finale at home against a surging Detroit Lions team who were riding a six-game winning streak, Tampa lost decisively, but the game became infamous due to a huge blowup between Wyche and QB Trent Dilfer; it was later revealed that Wyche planned to pull Dilfer for young backup QB Casey Weldon regardless of how the game was going, triggering Dilfer’s furious reaction and also angering teammates of the very respected if inconsistent starter. Rumor also has it Wyche knowing he would be let go by new owners without a winning record after a 5–2 start, ordered the team to wear orange pants and orange shirts (which at the time, would have been a first to wear the same color top and bottom), but after several players refused to wear it, the idea was scrapped. New owner Malcolm Glazer decided Wyche’s tenure as coach was done, and started the search for the next coach of the Buccaneers, a search that would bring in coach Tony Dungy. Tampa was ready to move forward with the right leadership on a trajectory from “terrible” to “uneven but promising”.