Winchester signed with the Philadelphia Eagles as an undrafted free agent on August 11, 2013.

[4] On January 23, 2017, Winchester signed a five-year, $4.45 million contract extension with the Chiefs.

[5] On September 17, 2017, in Week 2 against the Eagles, Winchester forced a fumble on a Darren Sproles punt return.

The fumble was recovered by teammate Anthony Sherman and helped set up a field goal scoring drive.

[6] Winchester won Super Bowl LIV with the Chiefs after defeating the San Francisco 49ers 31–20.