He played for Hibernian, Peterhead, Lokomotiv Moscow, Barnsley, Tom Tomsk, Birmingham City, Greenock Morton and represented Scotland.

[5][6] A Hibernian youth graduate, he made his debut for the club under manager Alex McLeish in April 2001 as a substitute against Dundee,[7] his only appearance that season.

O'Connor formed a formidable partnership with Derek Riordan, and between them they scored 42 goals that season, as Hibs earned qualification for the UEFA Cup.

[13] The extra-time goal, coming in the 109th minute, was enough to seal a 1–0 victory for the railway team, and provided a measure of redemption for O'Connor, who had struggled to settle in Russia for family reasons.

[13][6] O'Connor completed a £2.7 million move to Birmingham City on 28 June 2007,[14] and scored his first goal for the club on his first appearance, on 15 August 2007 against Sunderland in a 2–2 draw.

[18] O'Connor worked with a fitness coach over the summer, lost weight, and returned to training with a positive attitude towards the coming season and towards his manager.

[24] He returned to first-team action against Doncaster on 14 March 2009,[25] and his goal on 6 April that confirmed a 2–0 win over Championship leaders Wolverhampton Wanderers for a Birmingham side reduced to ten men was voted as the club's Moment of the Season.

[28] McLeish suggested that the injury dated back to O'Connor's time with Hibernian and had been aggravated by playing on synthetic pitches in Russia while he was with Lokomotiv Moscow.

[31] Although Birmingham were happy for the player to remain at Barnsley, whose manager wanted to extend the loan, budgetary considerations made it impossible.

[32] Though O'Connor returned to Birmingham's first team, Cameron Jerome's recovery from injury left the player again looking for regular football, so in November he rejoined Barnsley for another month.

[5] O'Connor's contract with Hibs expired on 1 June 2012; on the same day, he was found guilty on charges of possessing cocaine and obstructing a police officer.

[54] After featuring in the 1–0 victory against France at Hampden Park on 7 October 2006,[55] O'Connor and the rest of the team were given an evening off before reconvening ahead of the trip to Ukraine for another qualifying match.

Initially drafted in due to squad call-offs, O'Connor was given a place in the starting line-up for the friendly match with Austria and scored the only goal of the game.

[59] After appearing against Ukraine in October 2007, O'Connor was left out of the Scotland squad for almost two years, was recalled for the matches in September 2009 against Macedonia and the Netherlands after Kevin Kyle withdrew due to injury.

The programme charted O'Connor's career and explored his troubles with substance abuse, mental health issues and early retirement from football.

Whilst being interviewed for the programme, O'Connor revealed that he had considered suicide towards the end of his playing career, citing the love of his family and his responsibility towards his three children as motivation for seeking help through mental health counselling.