Season 1999-2000 would be one of the most memorable for Dumbarton, but not because of any titles won or lost, but because this would be the last season that the club would play at their famous Boghead Park. Dumbarton's home had been here for the past 121 years - the longest that any British football club had stayed at any home ground. Now the ground had been sold and Dumbarton would move to a new purpose built stadium at the foot of Dumbarton Rock.
The season itself was unremarkable. Three promotion places were up for grabs due to the addition of Elgin City and Peterhead the following season, however despite an encouraging start there was never a real chance of a top three finish and in the end a midtable 6th place was achieved. It would be the final game however that would define the whole campaign. As it was a crowd in excess of 3,000 turned out to bid farewell to the old ground and with it a fine victory over promoted East Fife.
In the national cup competitions, there was little to cheer. In the Scottish Cup, Dumbarton lost to Stenhousemuir in the second round.
In the League Cup, after a win over Brechin City, Dundee would easily dispatch Dumbarton in the second round.
With newfound sponsorship, the Scottish Challenge Cup was re-instated, but the same old failures beset Dumbarton - yet another first round defeat, this time to Airdrie.
Locally, in the Stirlingshire Cup, Dumbarton lost their two group ties.
Source: "1999-2000 Third Division - SPFL Archive". SPFL (in Malay). Retrieved 29 April 2021. Rules for classification: 1) points; 2) goal difference; 3) number of goals scored.
Dumbarton played an under 19 team in the Scottish Youth Division B, and with 6 wins and 4 draws from 26 games, finished 9th of 10.
Trivia
The League match against Albion Rovers on 8 August marked Kenny Meechan's 100th appearance for Dumbarton in all national competitions - the 114th Dumbarton player to reach this milestone.