Regan joined the Jets as part of the youth system in 2008 from state league club Azzurri Football Club. He captained the team and played primarily as a center back. On 3 June 2010 his strong performances were rewarded with a one-year contract. He was signed primarily to cover seasoned center backs Nikolai Topor-Stanley and Ljubo Miličević.
Taylor Regan made his Debut on 16 October 2010 in Round 10 against Brisbane Roar.
The Match finished 1–1 and Regan was a standout performer, gaining praise from coaches and senior players. An award chosen by former greats of the club
In early February 2015, Regan was made captain of the Newcastle Jets by coach Philosophy Stubbins following the mid-season sackings of several players for disciplinary reasons. Regan left the Jets at the conclusion of the 2014-2015 A-League season, after being told his contract would not be renewed, following a tumultuous period at the club both and off the field in which the Jets finished last on the ladder.
In early December 2015 it was revealed that Regan had signed with Negeri Sembilan FA in the Malaysia Premier League for the 2016 season.
At the clubs Season Launch on January 12, Regan was announced as Captain for the upcoming season.