Lester played his schoolboy football at Leicester Celtic alongside the likes of Andy Reid, Barry Roche and Declan Field.
His performances attracted cross-channel clubs and he played for West Ham United in the famous Northern Ireland Milk Cup winning the Player of the Tournament award.
He began well and regularly played for the reserve team at the age of 16 but in his 2nd season, he broke his leg and missed the remainder of the year.
[2] His time on Merseyside was never the same after the broken leg and he returned home to Dublin and signed for Pete Mahon's Bohemians, making his League of Ireland debut as a substitute against Galway United on 31 August 2001.
In July 2017, Lester moved to the Leinster Senior League to join Greystones United, however only two months later he returned to Sheriff Y.C.