In 2003 and 2004, he attended Rangeview Intermediate School. Foreign high school, he attended Mount Albert Grammar School where he graduated Year 12 in 2009. In 2010, he attended Fraser High School in Hamilton, New Zealand for one final year where he was a member of Fraser"s national championship-winning team
Born in Auckland, Bailey played both rugby and basketball in primary school. As a junior, Bailey played in the Conference Basketball League for the Japan Tourist Bureau/Breakers in 2008 and for the Waikato Titans in 2010. New Zealand NBL
On 22 December 2010, Bailey signed a two-year deal with the Manawatu Jets of the New Zealand National Basketball League.
In his rookie season for the Jets, he averaged 4.8 points and 5.2 rebounds in 17 games.
In December 2011, Bailey left the Manawatu Jets, opting out of the second year of his two-year contract due to family and work commitments. He also desired to move back to Auckland.
Later that month, he signed with the Auckland Pirates for the 2012 New Zealand NBL season. In January 2013, Bailey signed with the re-established Super City Rangers for the 2013 New Zealand NBL season.
He subsequently had a breakout season playing for the young Rangers squad as he averaged 11.8 points and 7.8 rebounds in 15 games.
On 18 December 2013, Bailey re-signed with the Super City Rangers for the 2014 New Zealand NBL season. He averaged career-highs in points (194), rebounds (93) and assists (18) in 2014, as the Rangers improved from last in 2013, to seventh in 2014. Bailey and teammate Jason Cadee were the driving force behind the Rangers resurgence.
On 1 November 2014, Bailey signed with the Southland Sharks for the 2015 New Zealand NBL season.
In 20 games for the Sharks in 2015, he averaged 10.0 points, 6.8 rebounds and 1.5 assists per game. On 7 September 2015, Bailey re-signed with the Southland Sharks on a two-year deal.
New Zealand Breakers
In August 2013, Bailey signed with the New Zealand Breakers as a development player for the 2013-2014 NBL season. On 28 October 2013, Bailey was elevated to the Breakers" tenth roster spot following the addition of Gary Wilkinson and the release of Darnell Lazare and Jeremiah Trueman.
Despite the elevation, he only managed to appear in five games, scoring a total of six points.
On 9 July 2014, Bailey signed a one-year deal (with the option of a second) with the Breakers. On 29 April 2015, the Breakers exercised the team option on Bailey"s contract, re-signing him for the 2015-2016 season. On 20 October 2015, Bailey was released by the Breakers to make way for Corey Webster, who returned from a stint in the National Basketball Association. He appeared in three out of the Breakers first four games of the season, recording two points and five rebounds.
Plymouth Raiders
On 9 November 2015, Bailey signed with the Plymouth Raiders for the rest of the 2015-2016 British Basketball League season.
Bailey and his partner, Ashley, have two children together.
He won a championship with the Pirates in 2012, and averaged 3.9 points and 3.5 rebounds in 15 games. As the team"s starting small forward, he was a consistent role player and was great on defense, helping his team finish the regular season with a 15–3 win/loss record. He and fellow starting five members Kevin Braswell, Todd Blanchfield, Adrian Majstrovich and Tai Wesley dominated the season, going on to win the 2015 championship with a 72–68 grand final win over the Wellington Saints. Gaining a full roster spot for the 2014-2015 season earned Bailey more playing time as he appeared in 27 games, averaging 2.0 points and 1.2 rebounds, and in the process became an Australian NBL champion after the Breakers defeated the Cairns Taipans 2–1 in the best-of-three grand final series.
