On 30 July 2019, Cutrone joined Wolverhampton Wanderers on a four-year contract. Cutrone made his league debut for Wolves as a substitute in their opening Premier League fixture of the 2019–20 season, a 0–0 away draw with Leicester City on 11 August, having made his debut appearance (also as a substitute) in the club's 2019–20 UEFA Europa League match away to FC Pyunik of Armenia three days earlier. On 15 August, Cutrone made his full debut for Wolves in a 4–0 home win against FC Pyunik in the 2nd Leg of the UEFA Europa League Third Qualifying Round. Cutrone made his full Premier League debut for Wolves in a 3–2 away defeat to Everton on 1 September. His first goal for Wolves came on 14 September, in a 2–5 home loss to Chelsea in the Premier League. In a 2–0 home success against West Ham United on 4 December 2019, Cutrone scored having only been on the pitch for two minutes as an 84th minute substitute.