Winfield Jr. attended Eden Prairie High School in Eden Prairie, Minnesota for his freshman year before he and his family moved to The Woodlands, Texas and attended The Woodlands High School, where he was a three-year letterer and two-year starting safety, in addition to being the team's kick returner, playing alongside future NFL players Ethan Bonner and Patrick Carr.

[1] Winfield was considered a two-star recruit by Rivals.com, and accepted a scholarship from Minnesota over offers from Baylor, Eastern Michigan, Houston, Lamar, Missouri, South Florida, Texas State, and Wyoming, among others.

[18] He made his professional regular season debut in the Buccaneers' Week 1 season-opener during a 34–23 loss at the New Orleans Saints, recording six combined tackles (three solo) and a pass deflection.

[20] He was named the NFL Defensive Rookie of the Month for September (23 total tackles, two pass deflections, two sacks, and a forced fumble from Weeks 1–3).

[22] In Week 14, Winfield led the team with a season-high 12 combined tackles (ten solo) and had a sack on Kirk Cousins during a 26–14 win against the Minnesota Vikings.

On January 9, 2021, Winfield started in his first career playoff appearance and recorded six combined tackles during a 31–23 victory at the Washington Football Team in the In the Wild Card Game.

[26] On January 17, 2021, Winfield had six combined tackles (five solo) and forced a fumble by tight end Jared Cook that was recovered by Devin White as the Buccaneers earned a 30–20 victory at the New Orleans Saints in the Divisional Round.

[27] During practice prior to the National Football Conference (NFC) Championship Winfield sustained an ankle injury and was subsequently inactive as the Buccaneers defeated the Green Bay Packers 31–26.

On January 16, 2022, Winfield recorded five combined tackles (three solo) and a sack on Jalen Hurts during a 31–15 victory against the Philadelphia Eagles in the Wild Card Game.

[33] On January 26, 2022, Winfield earned his first career Pro Bowl selection after being named as an injury replacement for Seattle Seahawks safety Quandre Diggs.

[35] On March 30, 2022, the Tampa Bay Buccaneers promoted defensive coordinator Todd Bowles to head coach after Bruce Arians retired and shifted to a senior football consultant role.

He completed the 2022 NFL season with 80 combined tackles (64 solo), a career-high four sacks, one interception, three passes defended, and one forced fumble in 13 games and 13 starts.

He ended the season with a total of 60 combined tackles (34 solo), three pass deflections, two sacks, one fumble recovery, and a touchdown in nine games and nine starts.