East Fife as champions of the 2007–08 season were directly promoted to the 2008–09 Scottish Second Division.
They were replaced by Berwick Rangers who finished bottom of the 2007–08 Scottish Second Division.
A second promotion place was available via a play-off tournament between the ninth-placed team of the 2007–08 Scottish Second Division, Cowdenbeath, and the sides ranked second, third and fourth in the 2007–08 Scottish Third Division, Stranraer, Montrose and Arbroath respectively.
[1]) The SFL voted on the matter on 3 July,[2] with 5 clubs having put forward applications.
Annan, who like Gretna are from the Dumfries and Galloway region, were chosen above other applicants Cove Rangers, Edinburgh City, Preston Athletic and Spartans.