Winfree first began his college career at the University of Maryland, where as a freshman, he finished the 2014 season with 158 receiving yards on 6 receptions. He was dismissed from the team due to an undisclosed code of conduct violation. He admitted to Coffeyville Community College for the 2015 season. After a year at Coffeyville, Winfree transferred to the University of Colorado. He did not play in 2016 due to a torn ACL he suffered from earlier off-season workouts. In 2017, he made his first NCAA appearance in three years, finishing the year with 325 receiving yards. During an injury-riddled 2018 season, he finished with 324 receiving yards.
On September 5, 2020, Winfree was waived by the Broncos.[5]
Green Bay Packers
On October 1, 2020, Winfree was signed to the practice squad of the Green Bay Packers.[6] He was elevated to the active roster on November 14 and December 12 for the team's weeks 10 and 14 games against the Jacksonville Jaguars and Detroit Lions, and reverted to the practice squad after each game.[7][8] On January 26, 2021, Winfree signed a reserves/futures contract with the Packers.[9]
On August 31, 2021, Packers released Winfree as part of their final roster cuts.[10] He was signed to the practice squad the next day.[11] He was elevated to the active roster on October 16, 2021, for the game against the Chicago Bears,[12] in which he played 2 snaps, but finished a game without a target. He was reverted to practice squad next day. He was elevated to the active roster again on October 28 ahead of a Week 8 game against the Arizona Cardinals,[13] during which he recorded his first NFL catch, a 12-yard pass from Aaron Rodgers. He finished the game with four catches for 30 yards. He was elevated to the active roster again on November 20 ahead of a Week 11 game against the Minnesota Vikings.[14] On December 14, 2021, the Packers signed Winfree to their active roster.[15] He was waived on August 30, 2022, and signed to the practice squad two days later.[16][17] He was elevated from the practice squad to the active roster on September 10, 2022.[18] He was elevated from the practice squad to the active roster on September 24, 2022.[19] He was elevated from the practice squad to the active roster on October 15, 2022.[20] His practice squad contract with the team expired after the season on January 8, 2023.
Indianapolis Colts
On May 9, 2023, Winfree signed with the Indianapolis Colts.[21] He was released on August 29, 2023, and re-signed to the practice squad.[22][23] He was promoted to the active roster on October 17, and was waived on December 9, 2023.[24] He was signed back to the practice squad on December 19 and promoted to the active roster on January 2, 2024.[25][26] He was placed on injured reserve on August 27, 2024.[27]
Winfree graduated from Academies at Englewood, a magnet sibling school to Dwight Morrow High School in Englewood, New Jersey. He received a Key to the City of Englewood from Mayor Michael Wildes on June 23, 2019, during an event at which his father announced the formation of Team Winfree Youth Foundation, a nonprofit that will host low-cost camps for football, soccer, and basketball, as well as leadership conferences for area youth.[28]