He joined Port Vale on a six-week loan spell in November 2011, though he did not make a first-team appearance.
He left Ipswich in January 2012 and subsequently had spells signed with Cork City, Shamrock Rovers, Portadown, Limerick, Cobh Ramblers, Waterford and Longford Town.
In July 2009, after a short trial O'Connor signed a one-year deal with Championship side Ipswich Town, who were managed by his boyhood hero, Roy Keane.
[6][7] O'Connor made his debut for Ipswich in the League Cup away against Shrewsbury Town, replacing Jack Ainsley as a substitute at half-time; the "Tractor Boys" went on to win the match on penalties following a 3–3 draw.
He played a further eleven league games for Ipswich in 2009–10; he impressed in midfield against Cardiff City,[9] though gave away a penalty in a draw at home to Doncaster Rovers.
[11] However, experienced player Mark Kennedy was also signed for a £75,000 fee, and was expected to battle O'Connor for the left-back spot.
He was then dropped from the first-team after suffering from a tore hamstring on international duty,[13][14] and did not play again until a three-game spell in December.
[15] However, he ruptured and dislocated his shoulder joint,[16] and so did not appear again until 25 January, in a 3–0 League Cup semi-final defeat to Arsenal at the Emirates Stadium.
I left something behind me and that's not an easy thing to come to terms with.He was linked with a move into Irish football, as both Dundalk and Shamrock Rovers expressed an interest in acquiring his services.
[28] He made his competitive debut for Rovers in the final of the 2012 Leinster Senior Cup, which ended in a 1–0 win over St Patrick's CY.
[18] He re-joined Cobh Ramblers in July 2018 and featured four times in the 2018 season, including an appearance in the 2018 League of Ireland Cup final defeat to Derry City at Brandywell Stadium; his penalty was saved by Gerard Doherty in the last kick of the game and the score ended as 3–1 to Derry.
[42] He made his debut appearance for the Republic of Ireland national under-21 team on 26 March 2011, in what ended as a 2–1 defeat to Portugal at the Estádio Municipal de Águeda; he was replaced by Ipswich teammate Conor Hourihane at half-time.