He played college football at Colorado, and was selected by the Denver Broncos in the sixth round of the 2019 NFL draft.
[1] 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.
Winfree was selected by the Denver Broncos in the sixth round (187th overall) of the 2019 NFL draft.
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 was elevated to the active roster again on November 20 ahead of a Week 11 game against the Minnesota Vikings.
[24] He was signed back to the practice squad on December 19 and promoted to the active roster on January 2, 2024.
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.