He now works as an analyst for Virgin Media Television (Ireland), BBC Radio 5 Live, BBC Match of the Day, Football Focus, Final Score, Ireland's Newstalk Radio Off The Ball football show and most recently for Canada's The Sports Network (TSN) and their coverage of FIFA World Cup 2022.

[citation needed] In December 1999, Peter Reid's Sunderland paid £2.5 million for the left winger, making him the third most expensive club signing at the time.

[citation needed] On the last day of the transfer window at the start of the 2003–04 season, Kilbane moved to Everton for just under £1 million, where he was reunited with David Moyes.

In return, he displayed great versatility which resulted in him being deployed right across the midfield, at left back or even as a support striker, as well has his preferred left-wing position.

[13] With limited first team opportunities at Wigan due to the emergence of Maynor Figueroa and with his contract set to expire in the summer, Kilbane transferred to Hull City on 15 January 2009 for an undisclosed fee believed to be in the region of £500,000,[14] signing a two-and-a-half-year deal with the Yorkshire club.

[16] On 1 January 2011, as the transfer window reopened, Kilbane joined Football League One side Huddersfield Town on loan until the end of the season, mainly as a replacement for the injured Damien Johnson.

[18] After signing for Huddersfield, he helped the team to a club record 26 league games unbeaten, before their eventual 3–0 defeat in the playoff final to Peterborough.

However, this run ended after he was not selected for Ireland's crunch UEFA Euro 2012 qualification tie against Slovakia due to a back operation.

[39] In 2020, Kilbane competed in the twelfth series of Dancing on Ice, alongside partner Brianne Delcourt;[40] the couple were eliminated in Week 5.

After relocating to Canada with Delcourt, Kilbane took up a role as professional analyst on The Sports Network (TSN) during the COVID-delayed UEFA Euro 2020.

He is a patron of the Down's Syndrome Association, and in February 2015, sent a complaint to the FA over allegations that West Ham United supporters had sung a chant mocking the condition.

[41] Kilbane entered into a relationship with professional figure skater Brianne Delcourt, his skating partner on the twelfth series of Dancing on Ice.