They would remain in the bottom tier until their first-ever promotion eventually arrived under the club's legendary manager Alex McAnespie in 1993–94.

During Money's reign the club lifted the Scottish League Challenge Cup, defeating St Johnstone 1–0 at Broadwood on 3 November 1996.

The club, now under the management of Billy McLaren, then spent a further four years in the Second Division, with the most notable event being a strong Scottish Cup run in season 2002–03, which saw them go to the quarter finals, where they were beaten 4–0 by SPL side Motherwell.

On 21 January 2009, club chairman Nigel Redhead stated that Stranraer owed £250,000, and had a 50–50 chance of survival to the end of the season.

On 23 January 2009, as part of efforts to reduce costs to a manageable level, key player Gregory Tade transferred to Clyde.

Shortly after the game, Stranraer and team manager Derek Ferguson parted company by mutual consent and Keith Knox took over the reins.

[3] They secured their place in the third tier of Scottish football after a 2–1 win at Stenhousemuir on the final day of the season, but only after Stephen Aitken had taken over from Knox in October.

Aitken impressed to the extent that he was recruited by Championship side Dumbarton in May 2015 and was quickly replaced by former Ayr United manager Brian Reid.

2016–17 also started dreadfully for Stranraer and, following a 1–0 January defeat at Stenhousemuir which saw the hosts leapfrog the Blues at the foot of the table, Reid departed to be replaced by Stephen Farrell as manager.

Stranraer had a poor 2023–24 season, finishing bottom of Scottish League Two and facing East Kilbride in a two-legged promotion/relegation play-off.

A 2–2 draw away from home meant that Stranraer needed to win at Stair Park to avoid dropping into non-league football.

[6] In 1990, Stranraer became the first side to win a Scottish Cup tie on penalties, defeating Kilmarnock 4–3 after a 0–0 draw in the second round replay.