(Getty Images)

2000 – Tiger vs. Bob May at Valhalla

Two Southern California junior golf legends squared off, though Woods was already on his way to all-time-great status while May mostly toiled in his post-junior years after a successful college career. For one incredible round, followed by three playoff holes, May matched Woods and seemingly had the best of him multiple times. But Woods made several signature putts that remain on PGA Championship highlight reels. The duo tied the PGA Championship record for lowest score to par and shot back-nine 31s on Sunday. The win capped off a three-major season. Woods would win the 2001 Masters and hold all four major trophies. “I think it’s got to go down as one of the best duels in the game, in major championships,” Woods said.