Conway signed a two-year contract extension in September 2008 to extend his time at Tannadice until 2011. On 15 May 2010, Conway scored two goals in a man of the match performance as United beat Ross County 3–0 in the 2010 Scottish Cup Final. In April 2011, United manager Peter Houston indicated that he expected Conway to leave the club at the end of the season, due to the Terrors being unable to match his wage demands.