[3] He served in the English New Model Army in Scotland under General George Monck.

He accompanied Monck when he marched into England in 1660 at the head of his army and restored King Charles II to the throne.

Winthrop, remained in England and was in London in 1661 when his father presented his petition to obtain a charter for the establishment of a Connecticut colony.

He was a major in King Philip's War, and in July 1675, Winthrop requested Wombe, an Indian gunsmith captured by Ninigret, as a servant.

His funeral service was conducted by Cotton Mather, who called his sermon there Winthropi justa.