Cummings had a mercurial career, notable for his exceptional performances in his debut seasons at each of his clubs. The former West Australian from Swan Districts showed a capacity to kick goals from his first appearance with the Bombers when he bagged eight, but his coach Kevin Sheedy kept moving him around. Allowed to settle in the goal square at Port Adelaide, he showed strength and goal-sense and booted 70 goals for the year to top the club's goalkicking. The returns were more modest in 1998 and he found himself traded to the Eagles, where he won the Coleman Medal. Cummings struggled with form and injury in 2001 and again found himself discarded before being selected by Collingwood at the pre-season draft. However, injuries flared again and Cummings retired at the end of the 2002 season.