Although Charlton offered Randolph a new contract, he chose instead to join Scottish Premier League club Motherwell on 1 July 2010 on a free transfer. He signed a three-year-contract at Fir Park. Randolph made his Motherwell debut in the second qualifying round of the Europa League, in a 1–0 win over Icelandic side Breiðablik. The club were eliminated by Danish club OB in the play-off round; Motherwell complained to UEFA about OB fans throwing cigarette lighters at Randolph during the first leg. Randolph established himself as first-choice goalkeeper; in his first season, he broke John Ruddy's club record of 15 clean sheets on 27 February 2011 in a 2–0 win over Celtic. He helped Motherwell reach the 2011 Scottish Cup Final, but they lost 3–0 to Celtic; he suggested afterwards that Motherwell had been unlucky.