Gliddon attended Bunbury Senior High School in the coastal town of Bunbury, Western Australia, where he graduated from in 2008. He was twice named the Western Australia Player of the Year and played for the Australian Institute of Sport (AIS) during the 2007 SEABL season; in 17 games for the AIS, he averaged 7.1 points, 3.3 rebounds and 1.5 assists per game.
In 2008, Gliddon moved to the United States to attend Concordia University and play for the Eagles. As a freshman at Concordia in 2008–09, he finished second on the team for three-pointers made with 65. In 35 games (13 starts), he averaged 9.6 points, 2.8 rebounds, 1.7 assists and 1.3 steals per game. Following his freshman season, he returned to Bunbury and had a six-game stint with the South West Slammers of the State Basketball League. During that time, he averaged 10.3 points, 3.0 rebounds and 2.7 assists per game.
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. In 32 games (26 starts), he averaged 10.8 points, 1.9 rebounds, 1.0 assists and 1.1 steals per game.
As a junior in 2010–11, Gliddon recorded a career-high eight made three-pointers against Concordia Chicago on 29 December 2010. In 36 games (20 starts), he averaged 9.1 points, 2.0 rebounds, 1.6 assists and 1.1 steals per game.
As a senior in 2011–12, Gliddon led the Eagles to the NAIA national championship, going on to be named the All-Tournament MVP and to the All-Tournament Team, as well as the first-team All-NAIA D1. In 38 games (all starts), he averaged 14.6 points, 3.6 rebounds, 2.3 assists and 2.0 steals per game.
On 3 May 2012, Gliddon signed a three-year deal with the Cairns Taipans of the National Basketball League. Gliddon averaged 7.1 points, 4.0 rebounds and 2.8 assists in his first professional season. He also led the Taipans on the defensive end with 1.4 steals per game, ranking him third in the NBL. On 1 March 2013, he had a season-best game with a 26-point effort against the Perth Wildcats. For his efforts in 2012–13, Gliddon was named the recipient of the NBL Rookie of the Year Award.
On 15 March 2014, Gliddon was named the Taipans' MVP for the 2013–14 season. At 24, Gliddon became the youngest player to win the award since Nathan Jawai in 2008 at the age of 21. In 25 games on the season, Gliddon averaged 12.1 points, 3.0 rebounds and 2.9 assists per game.
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 season. Later that year, in October, Gliddon was named captain of the Taipans. He went on to lead the Taipans to a first-place finish in 2014–15 with a record of 21–7. After defeating the Perth Wildcats in the semi-finals, the Taipans reached the NBL Grand Final for just the second time in their history. They faced the New Zealand Breakers in the best-of-three series, but fell short, losing the series in straight sets. He appeared in all 32 games for the Taipans in 2014–15, averaging 10.5 points, 4.5 rebounds and 2.5 assists per game.
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 season. The Taipans dropped from first in 2014–15, to missing the playoffs in 2015–16, finishing the season with a 12–16 record. Gliddon appeared in all 28 games for the Taipans in 2015–16, averaging 13.5 points, 4.3 rebounds and 2.3 assists per game.
On 16 February 2016, Gliddon signed with AZS Koszalin for the rest of the 2015–16 PLK season. In 10 games for Koszalin, he averaged 7.2 points, 3.0 rebounds and 1.3 assists per game.
Gliddon returned to the Taipans for the 2016–17 season and helped them return to the playoffs, finishing the regular season in second place with a 15–13 record. They went on to lose to the third-seeded Perth Wildcats in the semi-finals, bowing out in straight sets. 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.
On 1 March 2017, Gliddon signed with Russian club Avtodor Saratov. He appeared in five games for Avtodor, averaging 1.4 points and 1.6 rebounds per game.
Gliddon is the son of Terry and Sue Gliddon, and has one brother, Michael, and two sisters, Ashleigh and Brittany.