Winfield plans to appeal the $7,500 fine for the hit on Cutler. Webb said Winfield tried to pull up to avoid a helmet-to-helmet hit.
The $10,000 uniform infraction apparently involved the height of Winfield's socks, according to the newspaper.
Winfield incurred the fine for contact on a Monday night play on which he blitzed Cutler. The 5-foot-9 Winfield's helmet struck the 6-foot-3 Cutler in the chin as he wrapped up the quarterback while they fell.
Cutler received three stitches to close the wound, but he returned and led the Bears to a 40-14 victory that clinched the NFC North title for Chicago.
Winfield has long been known as one of the NFL's most physical cornerbacks. But he is rarely fined for hits and is considered among the league's most fundamentally sound tacklers.
The Associated Press contributed to this report.