[1] Ballantyne was followed by Craig Barr and Brian McLean who turned down new deals, along with Grant Adam, Willie Dyer, Ross Perry, Michael Paton and Ryan Thomson who were released at the end of their contracts.

[10][11] Jordan Pettigrew became the club's third signing of the summer, joining from Livingston[12] and he was followed by midfielder Conor Scullion from Cumbernauld United[13] and forward Ryan Tierney from Edusport Academy.

[21] He made his debut the following day, in a 3–2 victory against Dundee United with all three goals coming from trialists - Muhammadu Faal, Joe McKee and Mati Zata.

On 11 July, just two days before the start of the Scottish League Cup, Duffy added four players: Mati Zata, Ruaridh Langan, PJ Crossan and Rico Quitongo to his squad.

[27] After a heavy defeat to Greenock Morton in the Scottish League Cup Duffy moved into the transfer market again - signing Joe McKee on a one-year deal.

The Sons recorded their first victory of the new season on 17 August, coming from 2–0 down to defeat Peterhead 3–2 at Balmoor Stadium thanks to goals from Ruaridh Langan, PJ Crossan and Isaac Layne.

[30] Tumility scored his first goal for the club in the afternoon, with Layne continuing his good from with a brace as Sons recorded a first home win of the campaign.

That was followed by a 2–2 draw with East Fife where Ryan McGeever scored his first goal for the club, with Isaac Layne taking his total to six for the season from the penalty spot.

[31] Frizzell made his debut in a 3–1 victory against Forfar Athletic where he scored twice, meaning that the Sons ended the first quarter of the season in fifth place with 13 points from their first nine games.

Two more positive results followed to ensure that the Sons ended the month undefeated, a 0–0 draw with Stranraer and a 1–0 victory against Peterhead with Ryan McGeever scoring his second goal of the campaign.

[32] A 2–0 home defeat to Montrose opened December, before a 4–3 comeback victory against Forfar Athletic where Sons had been 1–0, 2–1 and 3–2 down but came back to win with strikes from Joe McKee, Reghan Tumilty and a PJ Crossan brace.

Defender Jordan McMillan was next leave, joining Pollok on a short-term loan,[33] before the Sons defeated table-topping Raith Rovers at Stark's Park with goals from Crossan and Ryan McGeever.

January began with Mati Zata and Lewis Crawford being recalled from their loan spell with Rossvale[34] after an injury crisis left the duo as the only outfield substitutes for the 3–0 defeat to Falkirk.

[41] Jai Quitongo became the club's second signing of the winter, joining after leaving Persian Gulf Pro League side Machine Sazi.

[49] Having not played since early March, and with football suspended until at least June, the decision was taken to end the 2019–20 season on 15 April, with the Sons sitting sixth in Scottish League One.