The Como manager brought Alli into the fray as they sought an equaliser at the San Siro, replacing Lucas Da Cunha.
However, the 28-year-old Englishman was shown a red card for a clumsy challenge on former Chelsea midfielder Ruben Loftus-Cheek.
Referee Matteo Marchetti initially gave Alli a yellow card, but after a VAR review, upgraded it to a red. As Alli made his way off the pitch, his former Tottenham Hotspur teammate Kyle Walker, who joined Milan on loan from Manchester City in January, appealed to Marchetti for leniency.
Como had taken the lead through Da Cunha in the 33rd minute, only for the Frenchman to have a second goal disallowed by VAR after the break. Milan then flipped the Serie A encounter with goals from Christian Pulisic and Tijani Reinders, but Como continued to press for an equaliser.
Milan boss Sergio Conceicao brought on Loftus-Cheek for Rafael Leao shortly before Alli’s introduction.
The match also saw Cesc Fabregas receive a red card, leaving Como winless in their last three games.
Alli was signed by the Italian club on an 18-month contract in January, a move orchestrated by the former Arsenal, Chelsea and Barcelona midfield maestro.
He had been out of competitive action since his loan stint at Besiktas from Everton in the 2022/23 season was curtailed due to a hip injury sustained against Antalyaspor in February 2023.
The England midfielder’s woes continued with a groin injury that sidelined him for the entire last season before he became a free agent in the summer.
Despite these setbacks, Alli kept up his training with Everton and secured a deal through to 2026, with an option for an additional year, at Como after impressing during a trial.
Once hailed as one of England’s brightest midfield prospects, Alli opened up about his struggles with injuries, addiction, and mental health in a raw and candid interview with Gary Neville in the summer of 2023.
He disclosed a history of childhood sexual abuse, which visibly moved Neville to tears, and discussed his journey through rehab to overcome an addiction to sleeping pills.
By April 2024, appearing on Sky Sports’ Monday Night Football as a guest pundit, Alli expressed optimism about his recovery, mentioning he was beginning to “see the light” and felt “overwhelmed” by the positive reaction to his interview.
Fabregas, upon signing Alli, expressed confidence in his comeback, stating: “The club believes in Dele’s potential and is committed to helping him rediscover his best form.
“His experience and leadership qualities will undoubtedly benefit the squad.”