Gabbiadini was born in York, and played for his local team until the age of 18. In 1997, he moved to Sunderland, and went on to score 87 goals in 185 appearances for the Black Cats. During his time in the North East, he won the Third Division, and played in the Play-Off final in 1990, eventually securing promotion to the First Division when Swindon were refused promotion due to financial reasons. Gabbiadini enjoyed spells at Derby, Darlington, Northampton and Hartlepool before retirement.