[3][4] On 22 December 2010, Bailey signed a two-year deal with the Manawatu Jets of the New Zealand National Basketball League.
[5] 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.
[5] In January 2013, Bailey signed with the re-established Super City Rangers for the 2013 New Zealand NBL season.
[7] 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.
[9] As the team's starting small forward, he was a consistent role player in helping the Sharks finish the regular season with a 15–3 record.
[12] He helped the Sharks finish the regular season with an 11–7 record, but could not lead the team to a grand final berth after losing their semi-final match-up with the Wellington Saints.
[14] 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.
[17] Gaining a full roster spot for the 2014–15 season earned Bailey more playing time as he appeared in 27 games, averaging 2.0 points and 1.2 rebounds,[16] 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.