On 7 September 2015, Bailey re-signed with the Southland Sharks on a two-year deal. Due to his commitments with the Plymouth Raiders, Bailey missed the Sharks' first 10 games of the 2016 season, making his season debut on 22 April 2016 against the Taranaki Mountainairs. 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. In nine games for the Sharks in 2016, Bailey averaged 8.8 points, 6.1 rebounds and 1.6 assists per game.
