Born in
Hamilton, Ontario, Cupido began his junior lacrosse career with the
Hamilton Bengals in the Ontario Junior B league in 2007. He moved on to the Junior A
Six Nations Arrows in 2008. Cupido scored 57 goals and added 55 assists for the Arrows over three regular seasons and he finished his Junior A playoff career with 25 goals and 46 points. He was selected in the fifth round, 38th overall, by the
Colorado Mammoth in the 2011
NLL draft and in the fourth round, 22nd overall, by the
Kitchener-Waterloo Kodiaks in the 2012
MSL draft. Cupido appeared in only one game for Colorado in the 2012 season, but broke through in 2013 playing in all but the first regular season game and was named to the NLL All-Rookie team, leading the Mammoth and all NLL rookies with 101 loose balls. Cupido was named co-winner of the Most Valuable Defensive player in the MSL in 2014 for his play with the Kodiaks. He led the NLL in caused turnovers in 2015 and was the unanimous winner of the Transition Player of the Year award as voted by NLL writers. The NLL announced at their award ceremony in September 2015 that Cupido was the winner of the
National Lacrosse League Transition Player of the Year Award and a first team NLL All-Pro. He was a member of Team Canada for the
Heritage Cup in October 2017, scoring one goal in Canada's 19 to 6 victory over Team U.S.A. He led all defenders with 16 goals and tied for the NLL lead in short handed goals in 2018 and was once again named the Transition Player of the Year as voted by NLL writers, and the NLL Transition Player of the Year as awarded by the league. He was also named a first team NLL All-Pro for the 2017-2018 season. In June 2022, after winning an NLL championship with the Mammoth, he was traded to the Six Nations Chiefs by the Cobourg Kodiaks. A season ending Achilles injury cut short his 2023 season with the Mammoth. Cupido signed as a free agent with the Georgia Swarm in October 2024. == Football career ==