He has had stints in Serbia, Greece, Israel, China, Italy and Egypt, winning the 2023 BAL championship with Al Ahly.

[1] He moved to the United States in 2007 and played a season of college basketball for Lambuth University of the NAIA.

[3] In June 2008, Webster joined the New Zealand Breakers of the Australian NBL for the first time, signing as a development player.

[13][14] After re-signing with the Breakers on a three-year deal,[12] Webster's 2015 off-season saw him attend a pre-draft tryout with the Indiana Pacers[15] and later spent NBA preseason with the New Orleans Pelicans.

[16][17][18][19][20] With the Breakers in 2015–16,[21] Webster scored a career-high 39 points in November[22][23] and helped the team return to the NBL Grand Final series, where they lost to the Perth Wildcats.

[25] After missing the second half of the 2016–17 NBL season due to a hip injury,[26][27][28][29][30] Webster was released by the Breakers in March 2017.

[33] He started the 2018–19 NBL season strong,[34] but had a form slump in December[35] that saw him present as a shadow of the figure who was once a premier scorer in the league.

[36] He returned to form in the 2019–20 NBL season, averaging 19.5 points in 11 games, before being bought out of his contract in December in order to sign in China.

[46] On 12 December 2022, in his 250th NBL game, he hit the game-winning 3-pointer to lift the Wildcats to a 90–89 win over Melbourne United.

[68] He moved to Italy later that month to play for Virtus Roma of the Lega Basket Serie A,[69] but that season was also cut short due to the pandemic.

[71] In February 2023, Webster joined KK Mornar Bar of the Montenegrin League for the rest of the 2022–23 season.

[74] Webster joined the New Zealand national basketball team for the first time in 2008 at the FIBA Olympic Qualifying Tournament.