Cuggy was born in Walker, Northumberland and played youth football with Willington Athletic, where he was spotted by scouts from Sunderland. He joined the Roker Park club in March 1909 making his debut in a 3–2 defeat at Aston Villa on 12 February 1913. Sunderland narrowly missed out on the Double, losing the FA Cup final 1–0 to Aston Villa, who themselves were runners-up in the League.