| Club: | Dumbarton |
| Season: | 1958–1959 |
| Manager: | Peter McGown |
| Stadium: | Boghead Park, Dumbarton |
| League: | Scottish League Division 2 |
| League Result: | 4th |
| Cup1: | Scottish Cup |
| Cup1 Result: | Second Round |
| Cup2: | Scottish League Cup |
| Cup2 Result: | Prelims |
| League Topscorer: | Hugh Gallacher (23) |
| Season Topscorer: | Hugh Gallacher (26) |
| Prevseason: | 1957–58 |
| Nextseason: | 1959–60 |
The 1958–59 season was the 75th football season in which Dumbarton competed at a Scottish national level, entering the Scottish Football League, the Scottish Cup and the Scottish League Cup. In addition Dumbarton played in the Stirlingshire Cup.
See main article: 1958-59 Scottish Football League. This was to be another 'almost' season for Dumbarton in Division 2, but as in the previous campaign the final run-in was to be decisive with only one win taken from the last six games. It was to be 4th place again, with 45 points, 15 behind champions Ayr United.
See main article: 1958-59 Scottish League Cup. In the League Cup, qualification was there for the taking, with 3 wins and a draw from the first 5 games, but a final home defeat to Arbroath meant that Dumbarton would miss out again on progression.
See main article: article and 1958-59 Scottish Cup. In the Scottish Cup, after a good win over Highland League opposition, Division 1 opponents Kilmarnock were to prove to be too good for Dumbarton in the second round.
Locally Dumbarton lost out to Stenhousemuir in the semi-final of the Stirlingshire Cup.
Amongst the friendlies played during the season were three matches against English opposition - a 'home and away' tie against Accrington Stanley and an away trip to Colchester United.
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Source:[1]
Amongst those players joining and leaving the club were the following:
| Player | From | Date | |
|---|---|---|---|
| Jimmy Smillie | 9 Aug 1958 | ||
| John Bonnar | 23 Aug 1958 | ||
| Bobby Combe | 23 Sep 1958 |
| Player | To | Date | |
|---|---|---|---|
| Jimmy Smillie | Stenhousemuir | 14 Jan 1959 | |
| Bobby Gibson | Berwick Rangers | 24 Jan 1959 | |
| Con Murray | Forfar Ath | 30 Apr 1959 | |
| Ian Beveridge | Freed | 30 Apr 1959 | |
| John Bonnar | Freed | 30 Apr 1959 | |
| John McCall | Freed | 30 Apr 1959 |
Source:[2]
Dumbarton played a 'reserve' team in the Combined Reserve League. The season was split into two 'series' - with Dumbarton finishing runners up to Morton in the First Series (with 4 wins and 2 draws from 8 games) and winning the Second (with 6 wins from 8 games).
In addition, Dumbarton entered the Scottish Second XI Cup but were knocked out in the first round by Rangers.