Best known for his unusual double-handed forehand,[1] Gambill reached the quarterfinals of the 2000 Wimbledon Championships, the final of the 2001 Miami Masters, and won three singles titles.

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 run at Wimbledon in 2000 saw him beat Lleyton Hewitt, Fabrice Santoro, Paul Goldstein and Thomas Enqvist before losing to eventual champion Pete Sampras.

[4][5] Gambill played for the Boston Lobsters in the World Team Tennis league from 2008 onwards,[6] alongside other successful American players such as Andre Agassi, John Isner, and Robby Ginepri.

[4] In September 2009, Gambill reached the semifinals of the USA F23 Futures tournament (losing to second seed Michael McClune) in his first pro match of the year.