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Calleri scored a hat-trick for Espanyol in a Europa League match against Wolverhampton Wanderers on 27 February 2020; Espanyol won the match 3–2 but lost the two-legged tie by a score of 6–3.

On 26 August 2019, joined RCD Espanyol on a season-long loan deal.

On 22 August 2018, Calleri was loaned to fellow La Liga side Deportivo Alavés for one year.

On 11 July 2017, Calleri joined La Liga side UD Las Palmas on a one-year loan deal. He made his debut for the club on 18 August, starting in a 0–1 away loss against Valencia CF, and scored his first goal seven days later but in a 1–5 home loss against Atlético Madrid.

In January 2016, Calleri joined Uruguayan club Deportivo Maldonado. In an arrangement similar to a number of other players that have been registered to the club, he was loaned to the Brasileirão side São Paulo FC in the same month.

On 3 February 2016, Calleri made his debut and scored his first goal for São Paulo as they drew 1–1 with Universidad César Vallejo in the 2016 edition of Copa Libertadores.

On 13 July 2016, Calleri played his last match for São Paulo in a game they lost 1–2 against Atlético Nacional, in the Libertadores semifinals. He scored the only goal for São Paulo, in the 9th minute. Calleri said that it was his last game for the club and that he had "spent very beautiful six months" playing for Brazilian side. He ended the tournament as the top goalscorer, with 9 goals in 12 matches.

In August, West Ham United signed Calleri on a season-long loan. He made his Premier League debut coming off the bench in the match against Bournemouth on 21 August 2016. His only goal for the club came in the 94th minute in a 3–1 win against Middlesbrough at the Riverside Stadium on 21 January 2017. His full Premier League debut finally came on 22 April 2017 in a 0–0 draw with Everton at the London Stadium. He played 61 minutes before being replaced by Diafra Sakho. After 19 appearances with one goal scored, Calleri's loan ended.

Due to some impressive performances with Boca Juniors and São Paulo, Calleri earned a call-up to the Argentina Olympic squad for the 2016 Summer Olympics. On 29 July 2016, Calleri made his Argentina Olympic debut in a friendly against Mexico, which resulted in a 0–0 draw.

On 1 November 2015, Boca Juniors were crowned champions of the Argentine Primera División, in which Calleri scored 10 goals in 26 matches and achieved his first title as a professional player. Three days later, Boca Juniors won the 2014–15 Copa Argentina.

In July 2014, Calleri signed for Boca Juniors, with coach Carlos Bianchi deciding to take-up the right that the club had with the player, a holding of 30% of the player' rights.

On 27 July 2014, Calleri made his Boca debut in a 2–0 loss to Huracan. In the league, his debut came on 18 August as a substitute in a 1–0 win over Belgrano, and a week later coach Rodolfo Arruabarrena started Calleri for the first time in a 3–0 loss to Atlético Rafaela.

On 14 August 2013, Calleri debuted for All Boys against Estudiantes in the quarterfinals of 2012–13 Copa Argentina. He made his league debut on 7 September, against Argentinos Juniors, and played his first full game in his team's defeat against Godoy Cruz on 7 October.

Jonathan Calleri (Spanish pronunciation: [ˈɟʝonataŋ kaˈleɾi] ; Italian: [kalˈlɛːri, ˈkalleri] ; born 23 September 1993) is an Argentine professional footballer who plays as a striker for Spanish club RCD Espanyol on loan from Deportivo Maldonado.