Widely regarded as one of the greatest doubles tennis players of all time,[2] Bryan was ranked as the world No.

In 1998, he won the "Triple Crown" by taking the NCAA singles, doubles (with his twin brother Mike), and team titles.

In 2005, the Bryan brothers made it to the finals of all four Grand Slam tournaments, only the second time a men's doubles team has done this during the open era.

He underwent a hip relining and made a remarkable recovery, rejoining his brother less than a year later for the 2019 Australian Open and making it to the quarterfinals.

They went on to play for the Newport Beach Breakers in 2004, the Kansas City Explorers from 2005 to 2012, the Texas Wild in 2013, the San Diego Aviators in 2014, the California Dream in 2015, the Washington Kastles from 2016 to 2018, and most recently the Vegas Rollers in 2019.

It was announced that Bryan, along with Mike, will be joining the Vegas Rollers during the 2020 WTT season set to begin July 12 at The Greenbrier.

[citation needed] Together with his twin brother Mike Bryan, the pair has won the most Davis Cup matches of any doubles team for the United States.