1999 US Open – Men's Singles

Patrick Rafter was the two-time defending champion, but lost to Cédric Pioline in the first round after succumbing to shoulder tendinitis. Andre Agassi won the title, defeating Todd Martin 6–4, 6–7^(5–7), 6–7^(2–7), 6–3, 6–2 in the final. This win gave him the No. 1 ranking, and helped put an end to Pete Sampras' streak of six year-end No. 1 rankings.