He also played in the Football League for Tranmere Rovers, Wigan Athletic and Derby County, finishing his career in England with Non-league side Kidderminster Harriers.
During that campaign he had loan spells with Tranmere Rovers and Wigan Athletic, before finally exiting Ewood Park after nearly seven years to join Birmingham City on a free transfer on 24 December 2001.
Kenna was named Galway United manager (taking over from his former Republic of Ireland U21 international team-mate Tony Cousins) in a press conference on 21 April 2008.
[6] Galway were forced to rely on a lot of young inexperienced players, but as the season drew to a climax Kenna engendered a real team spirit in the side to the extent that over the last seven games United collected five wins, a draw and one loss.
His first competitive match was a 3–0 home defeat at the hands of his previous club whose new manager, Ian Foster, had been Kenna's assistant the season before.
Indifferent league form (which included two more defeats at the hands of Galway) combined with the fact that he was commuting between Dublin and the UK saw Kenna come under pressure from the St. Pat's fans quite quickly, but a run to the Fourth Qualifying Round of the Europa League (which included a victory over Russian side Krylia Sovetov) appeared to have weathered the storm.
However, a 2–0 loss at home to First Division Waterford United in the quarter final of the FAI Cup ultimately led to Kenna's resignation as St. Patrick's Athletic manager on 18 September 2009.