The former Monza No.1 joined Thiago Motta's side for £12million and has proven to be a bargain.
Di Gregorio, who was named Serie A's goalkeeper of the 2023/24 campaign in between the sticks for Monza, has continued his excellent performances.
His latest being against Manchester City, making two fantastic saves as Juve ran out 2-0 winners against the champions of England.
The first was against Erling Haaland as the Norwegian was beautifully slipped through by Kevin de Bruyne.
Haaland attempted a chip but the oncoming keeper shot up a firm hand to deflect the shot as he spread himself out.
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Di Gregorio's next highlight came as he acrobatically flew across goal to palm away a long-range effort from Ilkay Gundogan destined for the top corner.
"We said no to Liverpool in the summer to join the Juventus project," said Carlo Alberto Belloni, agent of the goalkeeper.
"He's working hard to continuously improve. He set up a gym at home so he can train on his days off. He has an incredible mentality, and his desire is to be part of a Juventus side that rewrites history and wins important trophies."
Instead, the Reds agreed a deal with Valencia to sign Georgia international goalkeeper Giorgi Mamardashvili, after he impressed at Euro 2024 in his nation's surprise run to the last-16.
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He will remain at the Spanish club for this season and will finally join the Reds ahead of the 2025/26 campaign.
The apparent move for Di Gregorio raises questions about what Liverpool had planned for current No.2 Caoimhin Kelleher.
The Republic of Ireland international made no secret of his desire to leave the club in the summer, if that's what he had to do to get more regular first-team football.
However, Liverpool refused to let him go despite multiple offers, and the decision paid off with Kelleher performing admirably and showing his ability during a recent spell when No.1 Alisson Becker was out injured.
There will be the same questions asked about Kelleher's future next summer, though, when Mamardashvili arrives.
Di Gregorio has kept nine clean sheets in 15 appearances since joining Juventus and has only conceded ten goals - performances which earned him a call up to the Italy national team for the first time.
He is yet to make his debut as he remained on the bench against Belgium and Israel, but an appearance is surely on the horizon if his form continues.
The Old Lady are currently sixth in the league despite not losing a game yet, a feat explained by their nine draws.
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Something the team must correct as fans are conditioned to success, once winning the league nine consecutive times.
The 27-year-old will be a key cog in Juve's push for their first league title in five years.
A small wait considering the last time they won the Champions League was in 1996.
Motta's side remain on their toes as they sit 14th holding a playoff spot, one they could easily slip out of if they are not cautious.