Following the playoff final loss to Annan Athletic the Sons released Joe McKee, Martin McNiff, John Gemmell, Ally Love, Stuart Carswell, Russell McLean and Edin Lynch on May 16.

Defenders Sean Crighton[11] and Greig Young[12] joined from Stenhousemuir and Raith Rovers respectively, along with midfielder James Hilton from Stranraer.

[15] In the Scottish League Cup the Sons were drawn in a section with Dundee, Inverness Caledonian Thistle, Airdrieonians and Bonnyrigg Rose.

[17] The squad returned for pre-season training on June 17, with goalkeeper Harry Broun signing a new season long deal the same day.

[21] The club's Scottish League Cup campaign began with a 2-0 defeat to Airdrieonians with the Diamonds scoring twice in the final four minutes.

[23] A 0-0 draw and penalty shootout victory against Bonnyrigg Rose followed, before the campaign concluded with a 3-1 loss to Scottish Premiership Dundee.

[24] The club's first league game of the season ended in a 1-1 draw with Bonnyrigg Rose on August 5, with Ryan Blair scoring Sons' goal.

Goals from Sean Crighton, Ross MacLean and James Hilton had the Sons 4-0 up at half-time before Matty Aitken's second-half brace.

A week later Michael Ruth scored his first goal for the club in a 3-1 Scottish Challenge Cup defeat to Kelty Hearts.

In the Scottish Cup the Sons were given a home tie against Highland Football League side Banks O' Dee.

In the second round of the Scottish Cup the Sons secured a dramatic 3-2 victory over Highland Football League Banks O' Dee.

[32] Both Ruth and Wallace were on target again a week later, with Matthew Shiels and Finlay Gray also scoring in a 4-0 home win against Bonnyrigg Rose.

It was confirmed after the game that defender Greig Young would require surgery for a serious injury sustained against Peterhead in September.

The month ended with a dramatic 5-4 extra time Scottish Cup victory over League One Annan Athletic.

[35] December opened with a 1-0 defeat to Stenhousemuir thanks to a deflected 87th minute James Berry strike, that left the Sons eight points off the top of the table.

The final home game of the year also saw the Sons score four - with an early Tony Wallace penalty making him the first Sons player since Stephen Dobbie in 2006 to score 10 goals prior to Christmas - an own goal and headers from Ryan Wallace and Aron Lynas only enough for a point against bottom of the table Clyde, who netted twice in injury time.

[38] On January 5, goalkeeper Patrick O'Neil returned to the club on a deal until the end of the season with Brett Long ruled out for the rest of the campaign.

[42] On January 15, winger Ross MacLean left the club on a leave of absence after a change in his working circumstances.

[47] On January 25 captain Mark Durnan and defender Greig Young, both of whom had spent large spells out of the team with injury, agreed new contracts until the summer of 2025.

The month ended with back-to-back draws, 0-0 away at Stranraer and 2-2 at home to Elgin City - in a game where Sons came back from 2-0 down, thanks to goals from Michael Ruth and James Graham.

All the goals came in the first leg, with Jinky Hilton and Tony Wallace on target in a 2-1 home win[65] - followed by a 0-0 draw at Forthbank Stadium.