Football League in season 1987–88, although they maintained their commitment to the South League by running a reserve side. They won promotion in their first season in the East League, and two years later won the Premier Division. They became one of the league's top sides and qualified for the Scottish Cup's early rounds on various occasions. Scottish Football League Annan applied to join the Scottish Football League in 2000, when two new clubs were admitted, but lost out to Peterhead and Elgin City. Following the demise of local rivals Gretna in 2008, Annan applied along with four other clubs to replace them in the Third Division. They were the successful candidate, being chosen due to the standard of their facilities, ahead of Cove Rangers, Spartans, Preston Athletic and Edinburgh City. Their first league match as a professional team ended in a 4–1 win over Cowdenbeath in the 2008–09 season. They finished 7th that season and 8th in the next season (however, they reached the semi-finals of the Scottish Challenge Cup). They were challenging for promotion to the Second Division in the 2010–11 season, their 3rd season in Scottish senior football. They finished 4th and qualified for the play-off final after a win over Alloa Athletic in play-off semi-finals (2–1, 0–0). They played Albion Rovers in the two-legged final, however, they lost the tie 4–3 on aggregate (1–3, 2–1), meaning that they missed out on promotion to the Second Division. After the first quarter of the 2011–12 season, Annan sat top of the league, three points clear. Also, for the second time since becoming SFL members in 2008, they reached the semi-finals of the 2011–12 Scottish Challenge Cup. Later as the season progressed Annan dropped points and fell into mid table; they would then finish the season in 6th place, 8 points off the play-off places and 28 points off first position. A 3–0 defeat to First Division Falkirk ended their hopes of a first Challenge Cup Final. During the 2012–13 season, Annan secured a 0–0 draw at home to Rangers on 15 September 2012, in what was the first-ever league meeting between the two sides. In the same season, on 9 March, Annan beat Rangers 2–1 at Ibrox, the first win for the club after the appointment of Jim Chapman as manager in January. A second-place finish in the newly named SPFL League Two the following season included the