Calabria received his first call-up to AC Milan's senior team ahead of the away game against Lazio played on 25 January 2015, but remained an unused substitute.

[6] At the start of the 2024–25 AC Milan season Calabria lost his place to new signing Emerson Royal, came under intense criticism for his performances, encountered difficulties with head coach Paulo Fonseca, who was eventually sacked on 29 December 2024, and with new head coach Sérgio Conceição whom he was nearly involved in a physical encounter with after Calabria kicked a bottle that struck Conceição.

[15][16] On 1 February 2025, Calabria left the AC Milan training camp in Milanello to join the Bologna team.

[17][18] On 3 February 2025, it was confirmed that Calabria had signed for Serie A side Bologna on loan until the end of the 2024–25 season.

On 9 November 2020, Calabria received his first call-up to the senior Italy national team from manager Roberto Mancini for three friendly matches against Estonia, Poland, and Bosnia and Herzegovina.