Regan joined the Jets as part of the youth system in 2008 from state league club Azzurri FC. 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. During the 12/13 season Regan made 20 appearances and was awarded the Ray Baartz medal as player of the season. An award chosen by former greats of the club. In 2015 Regan was presented with the Newcastle Jets Members Award for Player of the season.