[1] During the tournament, Winterton and his linemates Brenden Sirizzotti and Thomas Johnston combined for 42 points en route to the championship title.

[1] Upon returning from the tournament, Winterton found consistency playing alongside Arthur Kaliyev and Jan Myšák and finished the 2019–20 season with 12 goals and 11 assists in 53 games.

However, he suffered a shoulder injury during the Bulldogs 2021 preseason camp and subsequently missed the first half of the OHL season.

[12] He added 46 points through 37 regular-season games as he helped lead the Bulldogs to the J. Ross Robertson Cup finals.

After adding 19 points through the 2022 OHL playoffs, Winterton suffered a dislocated shoulder injury after scoring in Game 5 against the Windsor Spitfires.

[18] He was cut from training camp on September 29 and re-assigned to their American Hockey League (AHL) affiliate, the Coachella Valley Firebirds, to start the season.

[19] Winterton made his professional debut and found a steady place on the Firebirds second line with Shane Wright and Cameron Hughes.

[25] After participating in the Kraken's 2024 training camp, Winterton was re-assigned to the Coachella Valley Firebirds to start the 2024–25 season.

[27] Winterton played that night in a 6-3 loss to the Colorado Avalanche, where he failed to register a point through 09:28 minutes of ice time.