The 1890–91 season was the 18th Scottish football season in which Dumbarton competed at a national level, entering the inaugural Scottish Football League and the Scottish Cup. In addition Dumbarton played in the Dumbartonshire Cup, the League Charity Cup and the Greenock and District Charity Cup, winning each of them.

Season August The season began with an invitation to play in the Rangers FC Sports eleven-a-side tournament. On 2 August Dumbarton defeated St Mirren 2–0 in the semi-final, but lost out a week later to the hosts, Rangers, 4–1 in the final.

On 16 August the opening games in the inaugural Scottish Football League championship were played, and Dumbarton began their campaign with a home fixture against Cowlairs. The team lined up as McLeod (goal); Hannah and Watson (backs); Keir, Boyle and McMillan (half backs); and Bell, Hutcheson; Mair; Henderson and Taylor (forwards). Taylor scored Dumbarton's first ever league goal after 15 minutes, but shortly thereafter Cowlairs equalised. In the second half Cowlairs were kept hemmed in as the Sons hit every part of the woodwork but the ball would not go in. Taylor scored late on but it was ruled out for offside and the game ended at 1–1.

Football was included as part of the International Exhibition of Science, Art & Industry held in Edinburgh in 1890, and the third game held in this connection was between Dumbarton and Leith Athletic. Wilson from the second XI taking Hutcheson's place was the only change to the team. The game was held in good conditions apart from a strong wind blowing down the pitch meaning most of the play was confined to one end. In the first half the Sons played against the wind and with good defensive play reached the interval only one down. In the second half Dumbarton used the conditions to their advantage and two goals from Wilson and another from Mair gave Dumbarton a 3–1 win.Special ‘One Off’ Tournaments, Scottish Football Historical Archive, 9 July 2020. Retrieved 6 January 2022

Three days later, Dumbarton travelled to Cathkin Park, to play Third Lanark in a league fixture. Hutcheson returned to the side. Bell opened his account after 30 minutes but Thirds replied soon after, this being the score at half time. Taylor and Mair restored the Sons advantage and the game finished 3–1.

On 30 August Hearts came to Boghead to fulfil a league fixture. McNaught came in to replace Henderson in the front line and reserve player McDonald played for McMillan. Hearts were first to score but Bell with his third goal in three league games equalised matters just before half time. The Sons came out in the second half intent on pushing forward and goals from Bell and Mair secured a 3–1 win.

At the end of the month, Dumbarton sat in second place in the league with five points from three games, a point behind Rangers.

September Dumbarton were drawn away against Smithston Hibs in the first round of the Scottish Cup on 6 September, but as the opponents did not have a suitable standard of ground the match was switched to Boghead. Alex Miller took McDonald's place in the half back line, The Sons were firm favorites for this tie and were a goal ahead from McNaught within five minutes. In the end Dumbarton eased through with an 8–2 win.

The early pace setters in the league, Dumbarton and Rangers met on 13 September at Boghead, An unchanged side took the field, The Sons were quick off the mark and goals from Bell (2) and Mair had the home side well ahead by half time. Dumbarton continued to play strongly in the second half and defeated their rivals 5–1, Bell completing his hat-trick.

After a free week, it was back to Scottish Cup business on 27 September, with Hibernian being the opponents at Easter Road. McDonald came in for Hannah and McMillan returned and replaced Keir. The Sons were ahead within minutes and held a 3–1 lead at half time. In the second half it was all Dumbarton with a further six goals – Taylor completing his hat trick – and a final 9–1 scoreline.

October On 4 October Dumbarton entertained near neighbours Vale of Leven for their home league fixture. The team was unchanged. An own goal provided the Sons with the lead but despite having most of the play it was Vale that equalised before half time. The second half began in a similar fashion with the Vale keeper being tested repeatedly. Eventually the Vale's defence was broken and Dumbarton won the tie by 3–1.

A week later it was Abercorn who were the visitors to Boghead on league business, with the only change to the team being the return of Hannah to the defence. Taylor had the Sons two ahead by half time then in the second half Taylor completed his hat trick and a brace from Galbraith finished off a 5–1 thrashing.

Clydebank were drawn at Boghead to play Dumbarton in the third round of the Scottish Cup on 18 October. Dumbarton fielded an unchanged full strength eleven. Taylor (2) and McMillan had the Sons comfortably ahead by half time. A further two from Taylor and one from Bell completed the scoring for a 6–0 victory.

The return league fixture at Cowlairs was played on 25 October. Unfortunately Cowlairs ground was unavailable and the Northern club made their ground available for the tie. The Sons were again able to field their strongest team. The Dumbarton men spend most of the first half swarmed around the Cowlairs goal with scores resulting from three scrimmage and a Bell strike giving the Sons a 4–0 lead. The game was more even in the second half and Cowlairs got one back, only for Bell to get his second and Taylor (his 17th goal of the season) to make the final score 5–1.

So at the end of the month Dumbarton led the league with 13 points from 7 matches, 4 points ahead of Rangers with a game more played.

November Following a free week it was back to Scottish Cup business on 8 November, with a fourth round tie against Mossend Swifts at Boghead. The same eleven took to the field. The game was barely seconds old when Mossend scored, but within ten minutes the Sons had scored twice through McNaught to take the lead. Mossend then responded with two goals of their own before McMillan, Mair and Taylor gave Dumbarton a 5-3 half time lead. The second half saw the home side score two more for a final result of 7–3.

On 15 November, eight of the Dumbarton first XI - McLeod; Watson; McMillan; Boyle; Taylor; Galbraith; Mair and McNaught – were selected to play in the county side against Renfrewshire. A 3–1 win was recorded with Taylor scoring two goals and Mair the other.

After a walkover against Dumbarton Albion, Dumbarton played away in the second round of the Dumbartonshire Cup against Duntocher Harp on 22 November. One change was made to the team with Keir returning and Hannah dropping out. Bell Galbraith and Taylor had the Sons well ahead early in the first half, and at the interval the score stood in Dumbarton's favour by 4–2. With the wind and rain at their backs Dumbarton completely dominated in the second half and ran out winners by 10–2.

On 29 November it was to have been the fifth round home tie in the Scottish Cup against 5th KRV, but the referee ruled the pitch unplayable. Instead, they played a friendly, where late goals from Taylor and McMillan gave Dumbarton a 2–0 victory.

December The re-run of the postponed Scottish Cup tie against 5th KRV was played on 6 December. An unchanged side took to the field The Sons had little difficulty in breaching the KRV defence and were 6–0 up by half time - Taylor notching a hat-trick (his fourth of the season so far). A further two goals in the second half completed the scoring for an 8–0 victory.

The Dumbartonshire Cup semi-finals were played on 13 December with Dumbarton drawn at home to play Clydebank. Robertson came up from the seconds to give Bell a rest. The Bankies surprised the Sons by scoring first but by half time had turned things around by leading 2–1. A further two goals in the second half made the final score 4–1.

On 20 December, the biggest match of the season so far saw 10,000 spectators crammed into Boghead to witness Dumbarton play Celtic in the Scottish Cup quarter final. The team was back to full strength with the return of Bell. Snow covered the ground and despite the referee being happy for the game to be played Celtic lodged a protest. Mair had the Sons in front at half time and then Mair again and Bell in the second half completed a 3–0 victory. The protest was subsequently dismissed.

The final match of the year involved the away league fixture against Abercorn on 27 December. Once again the full squad was available to play. The Abbies started off the stronger and were ahead but Taylor got the equaliser before half time. Taylor scored again (his 25th of the season) to make the final score a 2–1.

So at the end of 1890, Dumbarton remained unbeaten – leading the league with 15 points from 8 games, six ahead of Rangers - and still going strong in both the national and county cups.

January On New Year's Day Dumbarton played in front of a 15,000 crowd at Celtic Park. The Sons played without Keir who was replaced by second XI man Stewart. The Celts were first to score but Dumbarton equalised before half time. No further scoring took place the result being a 1–1 draw which was all the more impressive as Stewart was lost to injury for most of the second half.

Two further friendlies were played on 2 and 3 January with easy wins being recorded against Arbroath (6–0 away) and Kings Park (8–3 home) respectively.

After a blank week on 17 January Dumbarton played Abercorn in the Scottish Cup semi-final at Boghead. The full first XI played with Keir returning to the squad. The Sons were soon ahead from a Galbraith goal and McNaught made it two by the interval. Bell got a third and while the Abbies scored late on, the game was won by 3–1 and Dumbarton were in the final.

On 24 January Dumbarton played their home league fixture against Cambuslang. Watson and Taylor were missing and replaced by Lang (Methlan Park) and Thompson (second XI). McNaught was first to score before Bell scored twice to give the Sons a 3–0 interval lead. Keir and then late on Thompson scored in the second half for an easy 5–0 win.

With no match on 31 January, Dumbarton still headed the league with 17 points from 9 matches.

February The 1891 Scottish Cup Final was played on 7 February at Hampden Park, pitting the odds on favorites unbeaten Dumbarton against the surprise package Hearts. Full strength Sons took to the field in front of an 11,000 crowd. Hearts were first to show and were ahead after 13 minutes and held that lead with ease till the interval. After a disappointing first half Dumbarton picked up a little in the second but in the end Hearts were worthy winners.

The following week saw Dumbarton playing in another cup final – this time for the county championship. The venue was Boghead against Vale of Leven and the Sons team was minus Galbraith his place taken by Thompson. Vale were in front after 3 minutes and as was the case in the Scottish final the Sons were finding it difficult to get into the game. In the second half however Dumbarton played to their best and after Mair equalised, Taylor, Bell and Mair again scored for a 4–1 win – lifting the cup for the third season in a row.Dumbarton v. Vale of Leven. The Glasgow Herald, 20 February 1891, scan via London Hearts Supporters Club

On 21 February Celtic visited Boghead on league duty. Lang and Hutcheson replaced McMillan and Mair in the Sons team. The game was fast and exciting throughout and Galbraith had Dumbarton ahead by half time. Celtic came back in the second half and equalised, and although Boyle had the home team ahead once more, the Celts had the final say the game ending a 2–2 draw.