[6] He received his first call into the first team squad for a league match versus Cardiff City on 28 September 1999 and made his professional debut when he replaced Andy Scott after 85 minutes of the 2–1 victory.
[7] He made regular appearances during January 2000,[7] but his season ended after he suffered a torn cartilage during a 2–0 home defeat by Wigan Athletic on 1 April.
[2] Kennedy joined Southern League Premier Division club Crawley Town on a permanent contract in March 2001.
[10][14] Kennedy signed for League of Wales high fliers Barry Town on 29 March 2001 and scored on his debut in a 7–1 win over Llanelli.
[10][13] He made seven appearances and scored one goal in what remained of the 2000–01 season as Barry achieved the League of Wales and Welsh Cup double.
[15] Kennedy made 17 appearances during the 2005–06 season,[15] with the club finishing fourth in the league and as runners-up to Haverfordwest County in the West Wales Senior Cup.
[3] During the 2013 off-season, Kennedy helped former Crystal Palace teammate and Republic of Ireland international Stephen Hunt back to fitness after his release from Wolverhampton Wanderers.
[20] During the 2013 off-season, Kennedy was named fitness coach at Tipperary Southern & District League Premier Division club Clonmel Town.