Having already won two PGA Tour titles that year, Calcavecchia produced his best golf when he needed it most, birdieing the 18th hole to take just 13 strokes over four play-off holes, an Open record.
It seemed like 13 would be the most he could take however to win, as competing against Greg Norman and Wayne Grady, Calcavecchia entered the final hole of the play-off tied for the lead with the powerhouse Norman, who had shot 64 earlier in the day.
But a fateful tee shot from Norman, and a stunning approach from the American, ensured the Claret Jug would be going back across the Atlantic Ocean for the first time in six years, the longest barren period for an American Champion since 1961.
To listen to Calcavecchia reminisce over the key moments of the play-off with BBC's Iain Carter, listen to The Open Conversation - Mark Calcavecchia here.