Playing for the Nepean Raiders, in 2008-09 he was a Canadian Junior Hockey League First All-Star Team and was the CJHL Top Prospect of the Year, and in 2009-10 he was CJHL Scholastic Player of the Year and was the MVP of the CJHL All-Star Game.[2][4] He won the fastest skater competition at the National Junior A All-Star competition.[4]
Calof opted to attended Princeton University, where he played with the Princeton Tigers men's ice hockey team which competed in NCAA's Division I in the ECAC Hockey conference for four seasons. In his freshman year (2010–11), Calof was named the ECAC Rookie of the Year, to the ECAC All-Rookie Team, and ECAC Third All Star Team.[2] In 2011-12 he was All-Ivy League Second Team and in 2012–13 he was ECAC Second All-Star Team and All-Ivy League First Team.[2] He competed for Team Canada at the 2013 Maccabiah Games in Israel, winning a gold medal while averaging 2.0 points per game with 10 points on five goals and five assists in five games.[5][6]
Following his NCAA career, Calof continued his playing career signing with top Swedish club, Skellefteå AIK of the SHL. During the 2014–15 SHL season, Calof recorded 16 goals and 19 assists, gaining him attention for the SHL Rookie of the Year award.[7][8]
After claiming a second championships with the Lakers during his two season stint, Calof left the SHL and signed a one-year contract with German club, Schwenninger Wild Wings of the Deutsche Eishockey Liga (DEL) on May 18, 2022.[11] However before joining the club, Calof terminated his contract with the Wild Wings in order to sign a lucrative one-year contract to return to the KHL with Amur Khabarovsk on August 1, 2022.[12]
In the 2022–23 season, Calof made just 16 appearances with Amur in registering two points before opting to terminate his contract with the club on December 9, 2022. He would later join as a free agent Swiss club, Lausanne HC of the National League (NL), signing for the remainder of the season on February 16, 2023.[13] On March 13, Lausanne HC announced that they would not re-sign Calof.[14]