He entered the Middle Temple in 1656 and was called to the bar in 1660 and rose steadily, serving as counsel in various Parliamentary impeachments. In January 1672, he became attorney-general to the king's brother, the Duke of York and was knighted on 16 December 1672. He was appointed as Solicitor General in 1675 and chosen as MP for Windsor at a by-election in 1677 on the king's recommendation.
During the hysteria of the Popish Plot, his allegiances changed, and he participated in impeaching the Lord Danby. This led to his dismissal as Solicitor General. However he was elected as MP for Worcester in 1679 (twice) and again in 1681. While Parliament was not sitting, he defended political allies in the court and also the city he represented when its corporation was attacked by Quo warranto proceedings, as well as Oxford. His legal services remained in demand in the reign of James II of England. He was elected as MP for Tewkesbury in 1689, 1692 and 1695, though he had not initially sought the seat.
He married twice. By his first wife Elizabeth Herbert, he had a daughter Elizabeth who married Richard Dowdeswell of Bushbury MP. His second marriage was to Elizabeth, sister and coheir of Edward Salwey, who brought him Stanford Court at Stanford-on-Teme, Worcestershire to add to property he had already bought there with his considerable earnings. By her he had four sons and three daughters, including Salwey Winnington, Francis Winnington and Edward Winnington, later Jeffreys.