| Club: | Dumbarton |
| Season: | 1965–1966 |
| Manager: | Willie Toner |
| Stadium: | Boghead Park, Dumbarton |
| League: | Scottish League Division 2 |
| League Result: | 12th |
| Cup1: | Scottish Cup |
| Cup1 Result: | Third Round |
| Cup2: | Scottish League Cup |
| Cup2 Result: | Prelims |
| League Topscorer: | Jimmy Veitch (11) |
| Season Topscorer: | Jim Lynas/ Jimmy Veitch (14) |
| Prevseason: | 1964–65 |
| Nextseason: | 1966–67 |
The 1965–66 season was the 82nd 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 competed in the Stirlingshire Cup.
See main article: 1965–66 Scottish Football League. An uncharacteristically successful start to the league season, with only one defeat in the first ten games, saw Dumbarton at the top of the league at the end of October, and even with a winless 'blip' in November, another string of five wins on the trot followed, meaning that hopes were still high in February for that illusive promotion place. However, only 3 wins were taken from the final 16 games, and Dumbarton finished in a disappointing 12th place, with 35 points, 18 behind champions Ayr United.
See main article: 1965–66 Scottish League Cup. In the League Cup, Dumbarton maintained a 100% record at home in their sectional ties, but the three away defeats ensured no further progress to the knock out stages.
See main article: article and 1965–66 Scottish Cup. In the Scottish Cup, Dumbarton required to fight through two preliminary rounds, before disposing of Montrose and then Queen of the South. Aberdeen however were too tough a 'nut to crack' in the third round.
Locally, Dumbarton were unlucky in their attempt to retain the Stirlingshire Cup. A first round replay win over Division 1 opponents Falkirk was followed by a draw in the semi-final against Alloa Athletic. However the tie was decided by the toss of a coin - which Dumbarton lost.
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Source:[1]
Amongst those players joining and leaving the club were the following
| Player | From | Date | |
|---|---|---|---|
| Andy McBeth | Morton | 26 Jun 1965 | |
| John McCall | Airdrie | 1 Jul 1965 | |
| Billy Muir | Ayr United | 12 Aug 1965 | |
| Maurice Dunne | Our Lady's HS | 31 Aug 1965 | |
| Hugh McMahon | Kirkintilloch Rob Roy | 2 Oct 1965 | |
| Ally Miller | Berwick Rangers | 29 Oct 1965 | |
| Jim Lynas | Blantyre Victoria | 14 Jan 1966 |
| Player | To | Date | |
|---|---|---|---|
| Tommy Halliday | Morton | 17 May 1965 | |
| John McCall | Freed | 30 Apr 1966 | |
| Ally Miller | Freed | 30 Apr 1966 | |
| Billy Muir | Freed | 30 Apr 1966 | |
| Tommy Reynolds | Freed | 30 Apr 1966 | |
| Doug Robertson | Retired |
Source:[2]