[7] For the 2008–09 season, Gliddon moved to the United States to play college basketball for Concordia University.

[1] As a sophomore in 2009–10, Gliddon led the GSAC for three-pointers made with 85, as he tied for sixth-most in school single-season history.

[1] On 3 May 2012, Gliddon signed a three-year deal with the Cairns Taipans of the National Basketball League.

[8][9] He was not well known upon signing with the Taipans but quickly developed into a key player, playing all 28 games in the 2012–13 NBL season and breaking into the starting five.

[13] He was named the Taipans Club MVP, becoming the youngest player to win the award since Nathan Jawai in 2008.

[15] On 1 April 2014, Gliddon took up the option of the third year of his three-year contract, re-signing with the Taipans for the 2014–15 NBL season.

[17] He helped the Taipans clinch their first ever NBL minor premiership,[18] finishing the regular season in first place with a 21–7 record.

[21] On 27 March 2015, Gliddon re-signed with the Taipans on a three-year deal; the contract included a European out-clause after the 2015–16 NBL season.

Following the conclusion of the Taipans' season, Gliddon joined AZS Koszalin of the Polish Basketball League.

Gliddon once again appeared in every game on the season, averaging 10.6 points, 3.0 rebounds, 3.1 assists and 1.2 steals in 30 contests.

Following the conclusion of the Taipans' season, Gliddon joined Russian club Avtodor Saratov of the VTB United League.

[27] Gliddon finished in the Top 13 in the NBL's MVP voting,[28] and was named the Cairns Taipans co-MVP alongside Mitch McCarron.

[30][31] On 4 November 2018, he scored a career-high 30 points and hit the game-winning three-pointer with under a second left on the clock as the Bullets defeated the Adelaide 36ers 93–90.

He hit 638 three-pointers throughout his career, third most in the NBL's 40-minute era, trailing only Chris Goulding and Bryce Cotton.

[50] On 13 September 2024, Gliddon was appointed head coach of the Auckland Tuatara for the 2025 New Zealand NBL season.