 He was educated at Northwood School in Durban, Varsity College and the University of South Africa.He played for Durban Cricket Club and KwaZulu-Natal B and was a member of the Shell SA Academy in 2002 before leaving South Africa to play cricket in England.Dennington played for Orpington in the Kent Cricket League in 2002 and appeared for Kent County Cricket Club's Second XI during the season.