Calabria names two toughest Inter vs. Milan opponents from Primavera days

Former Milan full-back Davide Calabria has opened up about his experiences playing in the Derby della Madonnina, and has revealed which two players were his toughest opponents when playing against Inter for the Milan youth sides back in the day. 

The first Derby della Madonnina of the season will take place on Sunday evening. Inter are the designated home side, and currently sit at the top of the league table on 24 points. Milan, third on 22 points, have an opportunity to overtake their city rivals with a victory on Sunday. 

Calabria, who left Milan and joined Panathinaikos over the summer, took part in 19 derbies against Inter across his Rossoneri career, but that tally does not include the matches he played against the Nerazzurri in the youth sector. His first derby, in fact, came 11 years ago in 2014. 

Speaking in an interview with MilanistiChannel, Calabria revealed a special anecdote from his first match against Inter as a teenager. 

“The first was in the Primavera: It was January in 2014, Pippo Inzaghi was coaching us. We played at Interello and the Curva Sud came to sing and chant for us. As a kid, seeing those banners and hearing the support like that was a lot,” Calabria said. 

“We won 2-0, Benedicic and Di Molfetta scored the goals. I came on in the second half. Winning that derby in our opponents’ back yard, with our fans, made me feel like I was on cloud nine. That day I realised that the derby was the most beautiful game of all.” 

Calabria went on to explain that Inter’s Federico Dimarco, who is of the same age, has always been a tough opponent in the Derby della Madonnina. 

He also pointed to Cremonese’s Federico Bonazzoli as another of his toughest opponents in the Primavera days. The former Nerazzurri youth player has scored four goals from eight appearances in Serie A this season including the winner against the Rossoneri when he played against them in the first game of the 2025-26 season. 

“Those games were tough, played with a lot of heart. My toughest opponents were Dimarco, he was already really highly rated at youth level, and Bonazzoli – I see he hasn’t lost the habit of scoring goals against Milan yet.”