Winfield made his regular season debut in Week 1 during a 34–23 loss to the New Orleans Saints, recording 6 total tackles and 1 pass deflection. In Week 2, during a 31–17 win against the Carolina Panthers, Winfield recorded 11 total tackles as well as his first career sack on Teddy Bridgewater which resulted in a fumble that was recovered by teammate Jason Pierre-Paul. In Week 3, during a 28–10 win against the Denver Broncos, Winfield recorded 6 total tackles, 1 pass deflection, and a sack. On October 1, 2020, Winfield was named the NFL Defensive Rookie of the Month for his performance in September (23 total tackles, 2 pass deflections, 2 sacks, and 1 forced fumble from Weeks 1–3). In Week 7, during a 45–20 win against the Las Vegas Raiders, Winfield recorded 2 total tackles, 1 pass deflection, and his first career interception off of a pass thrown by Derek Carr.