He debuted in the National Basketball League (NBL) in 2002 with the Wellington Saints and won a championship with them the following year.

In 2013, he helped the NZ Maori team win the FIBA Oceania Pacific Championship while earning the tournament's most valuable player award.

[1][2] After spending the 2007–08 Australian NBL season as a training player with the West Sydney Razorbacks,[3] Bailey-Nowell returned to Taranaki in 2008 and played for the Mountainairs every year until 2017.

[4] In July 2020, he joined the Auckland Huskies for the rest of the 2020 NBL Showdown as an injury replacement for Taine Murray.

[10][11] In 2013, Bailey-Nowell played for the NZ Maori team in the FIBA Oceania Pacific Championship in Porirua.

[13][14] In June 2017, Bailey-Nowell travelled to France with the New Zealand 3x3 National Team to compete in the FIBA 3x3 World Cup.