Buffalo Bills – 1990
Scott Norwood singlehandedly crushed the Bills’ dreams in the 1990 playoffs against the Browns. He infamously kicked his field goal attempt ‘wide right’ as Buffalo crashed out of contention. This was one of the strongest rosters in their history with luminaries like Jim Kelly and Thurman Thomas on their books.
It’s no surprise that they entered the season as one of the most hyped NFL teams of the year. Heartbreakingly, the Bills bounced back and made four successive Super Bowl appearances without a single victory. This remains one of the most devastating legacies in NFL history (via UPI).