It was a cold and rainy day at Wimbledon on July 4th, 1999. But despite the somber weather that hovered over Centre Court, it was an unforgettable day—filled with pure joy—for Lindsay Davenport.

Federer lost his first ever match at Wimbledon against Jiri Novak in 1999 when he made his tournament debut as a wildcard. Novak, a Czech player who would reach a career-high ranking of world No 5 ...