He spent two years with Ipswich before returning to the Republic of Ireland to sign for former club Cork City.

[8][9] With Celtic he won a Scottish League Cup medal, playing in the team that beat Kilmarnock 3–0 at Hampden on 18 March 2001.

In December 2003 he broke his leg in a match against a former loan club, Coventry City after a challenge by Moroccan international Youssef Safri.

In October 2004, he broke his leg again soon after resuming training with Sunderland, after a tackle from then manager Mick McCarthy.

On 20 February 2007 he signed a two-year contract with hometown League of Ireland club Cork City, alongside former international colleague Gareth Farrelly.

Healy made his full Cork City debut against Bohemians when they were beaten in extra time in the Eircom League Cup Quarter Final held at Dalymount Park on 3 July 2007.

However, five days later, Hartlepool United manager Chris Turner confirmed that the deal had not happened due to late interest from Ipswich Town.

His most memorable moment came against St Patrick's Athletic in 2014 when he scored a late over head kick against a fellow title rival.

[19] Healy played and scored a goal against Australia at the FIFA World Youth Championship finals in Nigeria in 1999.

A succession of changes-of-heart by the Manchester United player led to the call-up being delayed and the deadline passing, with Healy unable to join the World Cup squad.