Born in Irvine, North Ayrshire, Troon resident O'Ware attended Queen Margaret Academy in Ayr.

After beginning his career with hometown team Troon Thistle boys club, O'Ware spent five years in the Rangers youth system at Murray Park, then a further two at Kilmarnock.

[1] He then signed for youth side Bonnyton Thistle,[2] where he was part of the team that won the Under-19 Scottish Cup final.

][citation needed] In January 2012, O'Ware suffered a stress fracture to his tibia making him miss at least a month of Morton's season.

[11] This form brought him to the attention of a host of Scottish Premiership clubs, and he was linked with a move to his boyhood heroes Celtic in the summer of 2017, as Brendan Rodgers looked to solidify his back line.

[15][16] On 25 August 2018, O'Ware was substituted four minutes into the game against Dundee United due to a knee injury,[17] and it was later revealed that he would miss the remainder of the season as a result.