Playing mostly at centre half-back, Madigan was a member of Hawthorn's 1989 VFL Grand Final winning side, in only his 6th league game. However, in the subsequent years he failed to establish his position in the Hawthorn team, playing ten or fewer games in each of his six seasons at Hawthorn.
In 1995 he was selected into the inaugural Fremantle Dockers squad with the second selection in the preseason draft. As one of the few players with AFL experience in the new expansion team, he managed the best season of his career, playing in 18 games. He remained with Fremantle for two more seasons, but struggled to keep his place, playing only 4 games in each of 1996 and 1997.
