1996–2005 Gambill began playing tennis at the age of five, looking up to multiple
Grand Slam singles titlists
Jimmy Connors and
John McEnroe. He has defeated, amongst other top players, former World No. 1s,
Roger Federer,
Carlos Moyá,
Lleyton Hewitt,
Gustavo Kuerten,
Marcelo Ríos,
Jim Courier,
Pete Sampras, and
Andre Agassi, as well as Grand Slam champions
Michael Chang,
Thomas Johansson,
Sergi Bruguera, and
Gastón Gaudio. His best performances at Grand Slams have been reaching the quarterfinals of Wimbledon in
2000 and the fourth round of the US Open in
2002. His run at Wimbledon in 2000 saw him beat
Lleyton Hewitt,
Fabrice Santoro,
Paul Goldstein and
Thomas Enqvist before losing to eventual champion
Pete Sampras. His run to the final of the
2001 Miami Masters included wins over Hewitt, Gaudio, and
Thomas Enqvist. He was coached by his father Chuck Gambill (1947–2020), who coached Jan-Michael's younger brother Torrey, who was also a professional tennis player. Throughout his career, Gambill was hampered by numerous injuries. Most prominently, while still in the world's top 40, he suffered a recurring shin condition, which severely limited him on the ATP Tour after 2004. He also started serving harder to try and compensate for lack of movement, which resulted in a shoulder injury.
Post–2005 Gambill played for the
Boston Lobsters in the
World Team Tennis league from 2008 onwards, alongside other successful American players such as
Andre Agassi,
John Isner, and
Robby Ginepri. As of 2020, he is currently in broadcasting and television as a Sports Analyst on the Tennis Channel. ==Personal life==