Van de Velde nearly pulled off an upset victory at the 1999 Open Championship at Carnoustie, when he was the clear leader playing the closing holes. He arrived at the 18th tee needing only a double-bogey six to become the first Frenchman since 1907 to win the tournament. He had played error-free golf for much of the week and birdied the 18th hole in two prior rounds.

Despite a three-shot lead, Van de Velde chose to use his driver off the tee, and proceeded to drive the ball to the right of the burn and was lucky to find land. Rather than laying up and hitting the green with his third, Van de Velde decided to go for the green with his second shot. His shot drifted right and hit the grandstands on the side of the green and bounced fifty yards backwards into knee deep rough.

On his third shot, Van de Velde's club got tangled in the rough on his downswing, and his ball flew into the Barry Burn. He removed his shoes and socks and gingerly stepped through shin-deep water as he debated whether to try to hit his ball out of the Barry Burn, which guards the 18th green. Ultimately, he took a drop and proceeded to hit his fifth shot into the greenside bunker. Van de Velde blasted to within six feet from the hole, and made the putt for a triple-bogey seven, dropping him into a three-way playoff with Justin Leonard and Paul Lawrie. Lawrie would eventually triumph in the playoff.