After starting with Deportivo Saprissa as a youth player from 2005 to 2010, Calvo moved to the United States to study at San Jacinto College after getting a scholarship and played football at university level during that period.

[3] On his return to Costa Rica in 2011, Calvo played for Herediano before a stint at Pérez Zeledón where he scored 5 goals in 21 matches.

[8] In 2018, Calvo was selected as an MLS All-Star, becoming the first Minnesota United player in club history to receive the honor.

[11] On 5 March 2022, Calvo scored two late set piece goals for a ten-man San Jose team to salvage a 3–3 draw at home against the Columbus Crew.

On 29 May 2011, Calvo made his debut with the Costa Rica senior team in San José in a friendly game against Nigeria.