Dumbarton had the chance to win late on from a penalty and while Ritchie scored, the kick was ordered to be retaken, and he was unable to repeat the task.

On 4 September Dumbarton commenced their Qualifying Cup campaign at Millburn Park against the current holders Vale of Leven.

Ritchie scored a second in the second half, and despite the Vale replying with a goal five minutes from time the Sons held on to win 2–1.

During the week Dumbarton signed former internationalist Finlay Speedie (ex Bradford Park Avenue) and goalkeeper Jim McCormick (ex Arthurlie) and both featured in the league match against St Bernards on 25 September at the Gymnasium.

Hynds made way for Speedie, while Gordon replaced Muirhead in the back line with Kane taking over at left half.

The Sons continued to press for a winner in the second half but were unable to break the Saints defence and were caught by a breakaway goal and lost by 2–1.

The game was a closely contested affair with only a single goal separating the teams – Ritchie (under the pseudonym Murray) scoring just before half time.

During the week Dumbarton had signed half back Willie Lithgow (ex Glasgow Perthshire) and forward David Anderson (ex Ayr).

In another tough tussle, the goals came in a five-minute spell just after the interval with Hill opening for the Sons and Abercorn equalising – the match ending in a 1–1 draw.

As October came to a close Dumbarton found themselves at the foot of the league table with 4 points from five matches played – but with games in hand over their nearest challengers.

Three changes were made to the team, Lithgow in the defence, Lipton in the half back line and Spence in the attack all returned.

The match turned out to be a disappointing one for Dumbarton as the Rovers left wing was in sparking form scoring a hat trick.

Dumbarton resumed league duty on 20 October with the return fixture against Vale of Leven at Millburn Park.

Vale continued to pressurise the Sons defence in the second half and took the lead, only for Speedie to equalise from a penalty kick.

Play switched to the other end and Lipton scored for Dumbarton but Ayr came back to equalise just before half time.

The home side were quickly into their stride and scored within five minutes, although Anderson then Brander had the Sons in the lead before half time.

Rovers lost a player due to injury and played the whole of the second half with 10 men, but Dumbarton failed to find a way through and the game ended in a 0–0 draw.

The final game of the year was a benefit for long-serving player Bob Gordon against Vale of Leven on 31 December.

Due to injury Raith played all of the second half with 10 men, but despite continued pressure their defence held firm, and late in the game scored a consolation goal from the penalty spot.

A week later Dumbarton faced their toughest challenge for a number of years as Celtic were the visitors in the first round of the Scottish Cup.

The Sons showed up well in the early stages and only a goalkeeping mistake by McCormick had the Celts a goal ahead at the interval.

So at the end of January Dumbarton continued to climb the league table – now in 7th place with 15 points from 14 matches played.

A bright start by the Sons was rewarded by an Alister Gordon goal and this lead was held till just before half time when Leith equalised.

Dumbarton's problems were increased when Ritchie retired from the field injured, and despite chances at both ends the game finished at 2–1 in favour of Leith.

In the second half Dumbarton also lost Ritchie to injury, but the nine men held out for a 1–0 win, with Cowdenbeath missing a late penalty.

Having already booked their place in the final Dumbarton played a couple of trialists and in the end lost their first game of the competition.

Leith Athletic won the Second Division title but decided not to put their names forward for election to the top fight.

Dumbarton, along with runners up Raith Rovers, Ayr and Abercorn went into the election together with Morton having finished second to bottom of the First Division.

Port Glasgow Athletic had finished at the bottom and resigned from the league with Raith taking their place – full results as follows: Source:[69]

Source:[70] In addition Edward Kane, John O'Neill and Daniel Forrester played their final 'first XI' games in Dumbarton colours.