Jimmy Connors was the first man to win 5 titles at the Flushing Meadows. The American picked up the wins in 1974, 1976, and 1978 followed by the back-to-back titles in 1982 and 1983
Pete Sampras was the second to match Connors' tally after winning the 2002 US Open. With wins in 1990, 1993, 1995 and 1996. The win in 2002 was the last ever appearance for the American retiring as the only man to win his final major.
Roger Federer matched the two Americans with his title at the 2008 US Open. The Swiss maestro won the title 5 years on the trot from 2004 to 2008. He narrowly missed out on a 6th consecutive title in 2009.
John McEnroe won 4 titles in Flushing Meadows during his glorious career in singles. He won a hattrick of titles from 1979 to 1981 before winning his 4th in 1984. He reached the final in 1985 as well but lost to Ivan Lendl in a repeat of the 1984 finals missing out on a record-matching 5th title.
Rafael Nadal completes the list with 4 titles to his name as well. The Spaniard picked up wins in 2010, 2013, 2017 and 2019 to become the second-most joint successful champ in New York.