Super Bowl: XXIII
Matchup: 49ers vs. Bengals
There's a reason they call Montana "Joe Cool." Super Bowl XXIII cemented the 49ers' quarterback as one of the all-time greats, as he led his team on a 92-yard scoring drive with almost no time left to deliver San Francisco its third title. Pinned back to his own eight-yard line, it took Montana 10 plays to get down to the Bengals' 10-yard line with just 39 seconds to play. His strike down the middle to John Taylor perfectly split two defenders, giving the 49ers the latest game-winning TD in Super Bowl history.