Since being elected into the Football League in 1927, Torquay United have yet to progress any further than the third tier of English football. United's highest ever League finish was when they were runners-up to Alf Ramsey's Ipswich Town in the Third Division South in 1957. After the Football League was expanded into four nationwide divisions in 1958, Torquay have spent most of their existence in the bottom section. However, United have won automatic promotion to the third division on three occasions (1960, 1966 and 2004) and promoted via the playoffs just once (in 1991). The 1991 Division Four play-off Final was the second time Torquay United had played at Wembley Stadium having been runners-up to Bolton Wanderers in the 1989 Sherpa Van Trophy Final. Torquay would make a third appearance at Wembley in 1998 but were beaten again by Colchester United in the Division Three play-off Final. Despite being relegated to the Football Conference in 2007, Torquay found themselves at the new Wembley Stadium the following year for the 2008 FA Trophy Final. Unfortunately, Torquay were destined to be the losing side again, being beaten this time by Ebbsfleet United. However, the club's fifth appearance at Wembley for the 2009 Conference National play-off Final resulted in a victory against Cambridge United and ensured the club's return to the Football League after a two-year absence.