Born in Togher, Cunningham was educated at Coláiste Iognáid Rís, representing the school in the Harty Cup.
He later attended University College Cork, with whom he won three Fitzgibbon Cup medals.
[1] Cunningham first came to prominence on the inter-county scene as a member of the Cork minor team in 1986.
Cunningham subsequently joined the Cork under-21 team, winning a Munster medal in 1991.
By this stage he had also joined his brother, Ger, on the Cork senior team, making his debut during the 1987-88 league.