He played college football for the Ohio State Buckeyes, earning consensus All-American honors and winning the Jim Thorpe Award.

[4] Head coach Wade Phillips named Winfield the third cornerback in the depth chart to begin the regular season, behind veterans Thomas Smith and Ken Irvin.

Winfield made his first career interception off a pass attempt by Colts’ quarterback Peyton Manning, that was originally intended for the wide receiver Jerome Pathon, and returned it for a three-yard gain in the fourth quarter.

[12] Winfield entered training camp slated as a starting cornerback after Thomas Smith departed during free agency and signed with the Chicago Bears.

Head coach Wade Phillips named Winfield and Ken Irvin the starting cornerbacks to begin the regular season.

On November 24, 2000, the Buffalo Bills placed Winfield on injured reserve after it was discovered he had a torn labrum cartilage in his right shoulder that would require surgery.

[15] Head coach Gregg Williams retained Winfield and Ken Irvin as the starting cornerbacks to begin the regular season.

[21] On November 23, 2003, Winfield recorded ten combined tackles (seven solo) and made his first career sack during a 17–14 loss against the Indianapolis Colts in Week 12.

[22] Winfield started in all 16 games in 2003 and recorded a career-high 107 combined tackles (92 solo), 11 pass deflections, two forced fumbles, one sack, and an interception.

[27] On October 17, 2004, Winfield recorded seven combined tackles, deflected a pass, and made his first interception as a member of the Vikings during a 38–31 win at the New Orleans Saints.

Winfield intercepted a pass by Saints’ quarterback Aaron Brooks, that was intended for wide receiver Ernie Conwell, and returned it for a 56-yard gain during the first quarter.

[30] Winfield finished the 2004 NFL season with 85 combined tackles (70 solo), five passes defenses, three interceptions, and two forced fumbles in 14 games and 14 starts.

[17] Head coach Mike Tice named Winfield and newly acquired free agent Fred Smoot the starting cornerbacks to begin 2005.

[33] In the Vikings' 30–27 win over the New Orleans Saints on Week 5 (October 6) of 2008, a Monday Night Football game, Winfield returned a blocked field goal attempt by Martin Gramatica 59 yards for a touchdown.