Riccardo joined Aston Villa at the age of 9 in 2005 and at 17 years old was part of the Villa U19 team that beat Chelsea in the 2012/13 NextGen Series, a competition that featured 24 highly ranked European teams including Celtic, Barcelona, Ajax, Juventus, PSG, PSV and Sporting Lisbon. He also made 4 appearances for the England U17 team in 2012
Between 2015 and 2017 he was loaned out to Dundee (where he made 11 apps), Doncaster (27) and Lincoln City (1) before signing a two year deal with Caley Thistle in July 2017
Calder had his contract terminated by the club on November 8th 2018