The following is a list of the men tennis players who have won the U.S. Open the most times in the Open Era. The Open Era began in 1968, when professional tennis players were finally allowed to compete at the four Grand Slam tennis tournaments.
Prior to the Open Era, Richard Sears, William Larned, and Bill Tilden all won the U.S. Open seven times each. A total that would rank at the top of this list, but Sears, Larned, and Tilden never competed against professional tennis players at the U.S. Open.
Tennis players who have won the U.S. Open the most times (Men)
T-1. Roger Federer - 5
So far in his career, Roger Federer has won five U.S. Open singles titles, and he won them consecutively from 2004 to 2008. Other players on this list have matched that win total, but none of them won five consecutive titles. From 2004 to 2009, Roger Federer won 40 consecutive matches at the U.S. Open, which is the most in a row all-time in the Open Era.
T-1. Pete Sampras - 5
Pete Sampras is tied with Roger Federer for the most singles titles ever at the U.S. Open (in the Open Era) with five. Pete Sampras won the U.S. Open in 1990, 1993, 1995, 1996, and 2002.
When he won the U.S. Open in 1990, Pete Sampras became the youngest male tennis player to ever win the U.S. Open (Open Era). The 12 year gap between his first win in 1990 and his last win in 2002 is the longest gap in the Open Era (Ken Rosewell had a 14-year gap between his first and last titles from 1956 to 1970).
With a killer serve that few players could handle, the hard-court surface at the U.S. Open was tailor-made for the power game of Pete Sampras. The long gap between his first and last wins at the U.S. Open shows that Pete Sampras was a top tennis player for well over a decade.
T-1. Jimmy Connors - 5
Jimmy Connors is tied with Roger Federer and Pete Sampras for the most U.S. Open titles in the Open Era with five (1974, 1976, 1978, 1982, 1983). Even though he is tied with Federer and Sampras, Jimmy Connors wins are more impressive because he won the U.S. Open on grass (1974), clay (1975), and hard court (1978, 1982, 1983) surfaces.
Jimmy Connors was one of the original bad boys of tennis. He would sometimes give umpires the finger and didn't mind yelling at the crowd, who usually rooted against him. It was funny to watch Connors at the end of his career busting his tail in night matches at the U.S. Open as a 40-year-old, with the crowd cheering him wildly on.
4. John McEnroe - 4
John McEnroe won four singles titles at the U.S. Open (1979-81, 1984). McEnroe had a bad reputation, and you can say whatever you want about him, but John McEnroe was one of the most entertaining tennis players of all-time.
5. Ivan Lendl - 3
Ivan Lendl won three consecutive U.S. Open titles from 1985 to 1987. Lendl made eight consecutive U.S. Open finals (1982-89) in singles play, which is the record for most consecutive finals in the U.S. Open.
T-6. Rafael Nadal - 2 (2010, 2013)
T-6. Patrick Rafter - 2 (1997, 1998)
T-6. Andre Agassi - 2 (1994, 1999)
T-6. Stefan Edberg - 2 (1991, 1992)