In 2003 Cupido had his best year to date. He booted 40 goals for the season in his small/medium forward role and was a very exciting and at times dominant player. Rex Hunt's 3AW radio call once said "Roll up, roll up, to the Hird and Cupido show" when the Essendon stars were on top of the game and demolishing the opposition. Cupido's kicking accuracy, run and foot-skills were sublime during 2003.
In 2004 Cupido had an indifferent year, suffering for most of the year with a knee injury. It was hoped he could bounce back in 2005, but it turned out he could not. At one stage early in the season, Cupido suffered a public blast from coach Kevin Sheedy in the media, and Cupido was not only dropped to the Bendigo Bombers in the VFL, but one level further, to the Bendigo reserves team. Eventually he fought his way back into the Essendon side but he never looked like recapturing his form. At the end of the 2005 season, Cupido was delisted from the Bombers.
Cupido continued his football career in the SANFL with South Adelaide Football Club in the 2006 season, hoping to get a second chance in the AFL via the 2007 Pre-season draft. He did not get picked in the draft after his first season and left South Adelaide to play for West Adelaide, where he was the club's leading goal scorer in 2007. In 2009, Cupido was stood down from West Adelaide to deal with a gambling problem. He played a total of 72 games in the SANFL; 51 with West Adelaide and 21 with South Adelaide.