[1] Milano was rated a three-star recruit by 247Sports and Rivals.com, receiving offers from Stony Brook, Miami University, Bowling Green, Arizona, Air Force and Boston College.

[4][5] Upon receiving the Westerman Family Flynn Fund Scholarship, Milano committed to Boston College, signing as early as July 2012.

[6] During his true freshman season in 2013, Milano first joined the field during the BC Eagle's season-opening home game defeating Villanova.

[12] Throughout training camp, Milano competed against veterans Ramon Humber and Gerald Hodges for the job as the starting weak side linebacker.

[13] Head coach Sean McDermott named Milano the backup weakside linebacker behind Humber to begin the regular season.

[15] He earned the start in place of strongside linebacker Ramon Humber, who was ruled inactive due to a broken hand suffered the previous week.

[17] His first career interception was off a pass attempt by Jameis Winston and he returned it 15 yards and received the game ball from head coach Sean McDermott.

[19] In the second quarter of that game, cornerback Leonard Johnson forced a fumble by Raiders' running back DeAndré Washington, that was recovered by Milano and returned 40 yards for a touchdown.

[21] On December 10, 2017, Milano was named the starting weakside linebacker over Humber and recorded a season-high 11 combined tackles in a 13–7 victory against the Indianapolis Colts.

[22] The next day, defensive coordinator Leslie Frazier stated Milano would remain the starting weakside linebacker barring any unforeseen circumstances.

[23][24] During a Week 17 matchup at the Miami Dolphins, Milano recorded six combined tackles, but ultimately left the 22–16 victory after suffering a hamstring injury.

[26][27] Milano finished his rookie season with 49 combined tackles (32 solo), two pass deflections, one interception, and a fumble recovery in 16 games and five starts.

[59] In Week 5 against the Jaguars, Milano suffered a season-ending fractured leg injury in the 25-20 loss and was placed on injured reserve on October 11, 2023.