In the 2009–10 season, Goodwillie began as a regular starter for United, scoring three goals in the first five matches of the season. Notching twelve goals by mid-April, Goodwillie's performances were recognised with the Scottish Premier League Young Player of the Year award. In May 2010, Goodwillie scored the opening goal as United won the 2010 Scottish Cup Final by 3–0 against Ross County.