1998–99 Dumbarton F.C. season

Indeed, up until the beginning of April it was still technically possible for Dumbarton to have gained promotion, but in the end ran out of games.

The winning run coincided with Ian Wallace's replacement by Jimmy Brown as manager, this following a suspension and subsequent internal investigation.

In the Scottish Cup, Dumbarton lost to Livingston after a creditable drawn match.

Note that due to the lack of sponsorship, the Scottish Challenge Cup was not played.

Locally, in the Stirlingshire Cup, Dumbarton managed a draw from two ties and thus failed to reach the final.