He is best known as one of the top doubles players in the world for most of the 1990s and into the early 2000s. His primary doubles partnerships were first with fellow Australian Mark Woodforde and later with Swede Jonas Björkman. Woodbridge and Woodforde are often referred to as "The Woodies" in the tennis world. Woodbridge also had a career high singles ranking of 19 after reaching the semifinals of Wimbledon in 1997, beating Patrick Rafter before losing to Pete Sampras. He did however have the distinction of being one of the few players to beat Sampras at Wimbledon, knocking him out in the first round in 1989.

Woodbridge's love of tennis was brought out by his family friend Beryl Taylor. As he progressed, he was coached by others, including Ray Ruffels and Desmond Tyson. Woodbridge was known for his "flatbat" style of tennis, where he would attempt to compensate for his lack of power by flattening the trajectory of the tennis ball over the net.[citation needed]

The Woodies won a record 61 ATP doubles titles as a team, including 11 Grand Slam events. After Woodforde retired from the tour in 2000, Woodbridge established a partnership with Björkman that resulted in five Grand Slam titles in four years. At the end of 2004, Björkman ended his partnership with Woodbridge. According to an interview Woodbridge granted to the Australian Broadcasting Corporation, Björkman wanted him to play more weeks on the tour, but Woodbridge wanted to limit his time away from his family as much as possible. Woodbridge then took on India's Mahesh Bhupathi as his new partner, who had just been dumped by Belarusian Max Mirnyi. Coincidently, Björkman and Mirnyi ended up partnering together.

In the 2000 Sydney Olympics, Woodbridge partnered with Woodforde to reach the final. In the fourth set tie-breaker against Canadians Sébastien Lareau and Daniel Nestor, Woodbridge served a double fault to lose the match.

Woodbridge was also a member of the Australian Davis Cup Team, playing the most ties (32) of any player.

Woodbridge announced his retirement at the 2005 Wimbledon Championships after 17 years as a tennis professional and 83 ATP tournament doubles titles, an all-time record. According to the ATP website, Woodbridge finished his career with US$10,095,245 in prize money.

In 2006 and 2007, Woodbridge joined the Seven Network's commentary team for the Australian Open.

He also became an ambassador for bowel cancer awareness group "Let's Beat Bowel Cancer". A Cabrini Health initiative.

In 2007, Woodbridge joined the 6th season of Dancing with the Stars, the Australian version.

In 2008 and 2009, Woodbridge aligned himself closely to the sailing community through his commitments at Hamilton Island Race Week hosting tennis clinics and wine tasting events.