McKenna began his footballing career as a youth team player at Northern Irish sides Enniskillen Town United and Ballinamallard United.
He joined Tottenham Hotspur as a youth player in 2002, after signing a scholarship contract with Spurs.[5]
He represented Northern Ireland at both under-19 and under-21 level. He was made captain of Northern Ireland’s under-19s side at the 2005 UEFA European Under-19 Championship by coach Mal Donaghy.[5]
In 2009, at the age of 22, McKenna retired from playing due to an ongoing hip injury which prevented him from making a senior first-team appearance for Tottenham.[4]
