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. In January 2013 he moved abroad to play for then Danish champions
Nordsjælland but he returned to Herediano in summer 2013. In January 2015, Calvo joined
Santos de Guápiles as a loan. In late May 2015, Calvo joined
Saprissa. In his first season with Saprissa, he appeared in 39 matches and scored five goals. The following season, he continued to be a set-piece threat as he scored 9 goals in 24 matches playing as a defender. On 27 December 2016, Calvo joined
Major League Soccer side
Minnesota United FC. In 2018, Calvo was selected as an MLS All-Star, becoming the first Minnesota United player in club history to receive the honor. On 3 May 2019, Calvo was traded to
Chicago Fire. Following the 2021 season, Calvo's contract option was declined by Chicago. On 26 January 2022, Calvo signed as a free agent with
San Jose Earthquakes. 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. This performance led to him being named in the MLS Team of the Week. He then moved to
Konyaspor in the Turkish
Süper Lig. On 15 January 2024, Calvo signed with
Juárez in Mexico. On 31 March 2024, he notches his first goal for the club by scoring a header contributing a 2–1 win against
Santos Laguna. On 5 August 2025, Calvo joined
Saudi Pro League club
Al-Ettifaq. ==International career==