See main article: 1999 US Open (tennis).
Andre Agassi defeated Todd Martin in the final, 6–4, 6–7(5–7), 6–7(2–7), 6–3, 6–2 to win the men's singles tennis title at the 1999 US Open. It was his second US Open title and fifth major title overall. With the win, Agassi returned to the world No. 1 singles ranking, ultimately ending Pete Sampras' record streak of six year-end No. 1 rankings.
Pat Rafter was the two-time defending champion, but lost to Cédric Pioline in the first round after succumbing to shoulder tendinitis.
See main article: 1999 US Open – Men's singles qualifying.