Harkes moved to Sheffield Wednesday of the English Football League in 1990. In a game that season against Derby County, his 35-yard blast glided into the net past former England World Cup goalkeeper Peter Shilton and earned him English football's "Goal of the Season" award. That season, Harkes became the third American (after Bill Regan for Romford F.C. in the 1948–49 FA Amateur Cup final and Mike Masters for Colchester United in the 1991-92 FA Trophy final) to play at Wembley Stadium when Sheffield Wednesday reached the 1991 League Cup final. There, the Second Division (now Football League Championship) Wednesday upset the First Division (now Premier League) side Manchester United 1–0. Also that year, Wednesday won promotion to the First Division.