San Diego Chargers vs Miami Dolphins
Jan 2, 1982, AFC Divisional Game
Orange Bowl, Miami, FL
Sports Illustrated dubbed this game as the "Game No One Should Have Lost". The game started out looking like it would be a San Diego rout as they jumped out to a 24 point lead. Miami pulled its starting QB Woodley and put in Don Strock, which jump-started the offense. Miami battled back to close to 24-17, the half ending on this Hall of Fame play:
In the second half, Miami managed to tie the game, but then San Diego's offense came back to life with Kellen Winslow putting on one of the great playoff performances by a TE (these numbers would be considered great in 2021), 13 receptions, 166 yards and a touchdown. Winslow also blocked a field goal attempt at the end of regulation that would have won the game for Miami. San Diego would block another Miami FG attempt in OT and ultimately would kick a FG to win the game 41-38. A picture of an exhausted Winslow being helped off the field by two teammates after the game is an enduring image in NFL lore and has been replayed constantly ever since.
The other one that hurts for me is Super Bowls XVII, where Miami lost to Washington mostly due to poor QB play by Woodley. The QB they needed that day (Dan Marino) would be drafted just 3 months later.