Scorer: Roy (78)
A strike from Annan Athletic’s Ally Roy 12 minutes from time proved decisive at The LIME Stadium at Stair Park.
The contest between Stranraer and their Dumfries and Galloway rivals looked to be heading for a goalless conclusion.
In the end, it was a goal that ensured Annan were celebrating their first three points of the campaign.
Stranraer boss Chris Aitken made three changes from the side that went down to Clyde last time out.
Finn Ecrepont and Mark McLuckie were brought into a reshuffled defence while Jordan Stuart came into the midfield.
That meant places on the bench for Kenzi Nair and Archie Traynor while Beejay Coll missed out through injury.
The recalled Stuart was the closest to an early opener for Stranraer as he battled well in midfield.
It then opened up for him but he pulled his shot wide of Charlie Albinson’s goal.
Aaron Healy curled an effort off target before Stuart saw one blocked following a corner.
However, the Blues could have been in front before the half time interval.
Healy’s through ball split the Annan defence but Aaron Quigg could then only fire just the wrong side of the post.
Stranraer again enjoyed chances early in the second half with Ronan Hughes finding Ecrepont.
The left back fired low across the goal but, again, it was off target.
The longer the game went on, the more it looked likely that one goal would be enough to decide the destination of three points.
That one goal arrived with just under quarter of an hour left to play.
Lewis Gillie and Zach Bruce challenged for the same ball and it broke kindly to Aidan Smith.
He floated a ball into the box and Roy had plenty of time to get his shot away.
Max Currie did well to make the save but it fell kindly for Roy to tuck home the rebound, despite the efforts of the retreating McLuckie.
Stranraer tried to put pressure on the Annan defence in the closing stages but Willie Gibson’s team kept them out.
The Blues return home next weekend for the league visit of Spartans, but before that, Aitken and his team will travel to Alloa Athletic looking for a win on Tuesday night in the KDM Evolution Trophy.
Stranraer: Currie, Dunne, Ecrepont, McLuckie, Gillie, Stuart (Dolan 52), Quigg, Healy (Traynor 80), Bruce, Hughes (Cleland 71), Dobbie.
Not used: Nair, Lynch, Cameron, McManus, Binnie and Henderson.
Annan Athletic: Albinson, Clark, Carrick, Gibson, McKnight, P Smith, A Smith, McDermott, Cooper, Roy (Connolly 86), Maxwell.
Not used: Martins, Bryson and Sliwinski.
Referee: Jordan Curran
Attendance: 457
HT: 0-0