On 12 July 2017, Di Gregorio and Alessandro Mattioli were signed by Serie C side Renate on a season-long loan deal. On 30 July he made his debut for Renate in the first round of Coppa Italia in a 3–1 home win over Siracusa. On 3 September, Di Gregorio made his Serie C debut for Renate and he kept his first clean sheet in a 3–0 home win over Padova. One week later he kept his second clean sheet in a 1–0 away win over FeralpiSalò. On 16 September, Di Gregorio kept his third clean sheet in a 3–0 away win over Modena. On 17 December, Di Gregorio kept his 10th clean sheet in a 1–0 home win over Pordenone. Di Gregorio ended his season-long loan to Renate with 38 appearances, 14 clean sheets, and 36 goals conceded.
On 4 July 2018, it was announced that Di Gregorio was loaned to a Serie B club Avellino. However, he did not play any matches for the team and returned to Internazionale. On 24 August 2018 he was loaned to Novara. On 30 September he made his Serie C debut for Novara in a 1–1 home draw against Juventus U23. On 7 October he kept his first clean sheet for Novara in a 3–0 away win over Piacenza. Three week later he kept his second clean sheet in a 2–0 away win over Pistoiese. On 18 November he kept his third clean sheet in a 0–0 away draw against Cuneo. On 12 December he was sent-off with a red card in the 90th minute of a 1–1 away draw against Alessandria. Di Gregorio ended his loan to Novara with 32 appearances, 12 clean sheets and 28 goals conceded.
Loan to Pordenone
On 10 July 2019, Di Gregorio was loaned to Serie B club Pordenone on a season-long loan deal. On 13 September he made his debut in Serie B for Pordenone and he kept his first clean sheet for the team in a 1–0 home win over Spezia. Three weeks later, on 5 October, he kept his second clean sheet in a 2–0 home win over Empoli and three more weeks later, on 26 October, he kept his third in a 0–0 home draw against Cittadella.
International career
Di Gregorio represented Italy only at Under-17 level. On 19 February 2014 he made his debut at U-17 level as a substitute replacing Emil Audero in the 59th minute of a 6–0 home win over Hungary U-17.
