[3] Annan Athletic's best finish in the SPFL was second in League Two in 2013–14 whilst its best result in the Scottish Cup is reaching the fifth round in 2021–22.

This proved an astute move when Annan Athletic won every competition they entered bar one in their first season in membership.

This switch, along with some upgrade work to their Galabank ground also allowed the club to compete in the qualifying stages of the Scottish Cup as well.

Annan applied to join the Scottish Football League in 2000, when two new clubs were admitted, but lost out to Peterhead and Elgin City.

They were the successful candidate, being chosen due to the standard of their facilities, ahead of Cove Rangers, Spartans, Preston Athletic and Edinburgh City.

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.

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.

[5] 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 clubs record points tally and saw them face Stirling Albion in the play-offs.

Forfar Athletic defeated Annan 6–4 on aggregate the following season in the play-offs, which signalled the end of Jim Chapmans reign.

Irishman Peter Murphy became only the third manager of Annan Athletic whilst an SPFL club, his first managerial role.

[7] The rivalry with Stranraer is less local but this has become an increasingly more competitive DG/A75 derby with many red cards seen in recent matches as the sides frequently meet in Scotland's fourth tier.