Born in Oldham, Greater Manchester, Wolfenden was a product of the Oldham Athletic youth system, having been with the club since the age of 9, Wolfenden made his first team appearance as a late substitute during a 1–0 defeat to Swindon Town in the then Second Division on 15 November 2003, making him the second youngest player to ever play for the Latics at the age of 16 years and 115 days.