Dumfries entered the Scottish Cup for the first time in 1889–90, losing 8–0 at Moffat in the first round.

The club's first competitive match at a local level, in the Southern Counties Charity Cup the same season, also ended in disaster.

[5] The following season the club had evidently improved; although it lost to Moffat in the Southern Counties Charity Cup, it was only by the remarkable score of 7–5,[6] and in the first round of the Scottish Cup the club hammered Newton Stewart Athletic F.C.

[9] The club's colours were black and white vertically striped shirts with "dark" (navy serge) knickers.

[10] For its final season as Dumfries St John's, the club changed the shirts to maroon.