During his time at Monza, Di Gregorio established himself as one of the best goalkeepers in Italy, standing out for his shot-stopping ability, his ability to keep clean sheets while producing many saves, stop penalties, and distribute the ball effectively and launch attacks; he was named the Serie A Best Goalkeeper of the 2023–24 season for his performances, and drew praise from former Juventus and Italy goalkeeper Gianluigi Buffon, even being touted as a potential successor to him at the Turin-based side. Upon signing with Juventus, his club profile described him as an "all-round goalkeeper," with a "modern" style, who possessed good reflexes and shot-stopping abilities, in addition to being adept at playing with his feet. During the latter half of his second season at the club, however, he suffered a decline in form, which led his shot-stopping ability to be brought into question by several pundits, in particular following a series of poor performances in Serie A and the Coppa Italia, which led him to be dropped from the starting line-up in favour of Mattia Perin.

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