[1] As a player, he played as a fly-half for Pontypridd RFC, the Cardiff Blues and the Ospreys.
Born in Cefn Hengoed, Caerphilly, Flanagan began his career as a junior with Ystrad Mynach.
That proved to be his annus mirabilis, as he played for Wales at under-21 level, made his regional debut for the Blues and also scored the game-winning drop goal in injury time at the end of the 2006 Welsh Cup final against Neath.
[2] After four years playing regional rugby with the Blues, Flanagan signed a three-year contract with the Ospreys for the 2010–11 season, where he would compete with Dan Biggar and James Hook as the team's starting fly-half.
[3] However, he left the Ospreys after just two years in July 2012,[4] and returned to Pontypridd.