1905-1906
There were 222 entries for this season’s competition. In anticipation of the 1st round draw, the Evening Telegraph reported that ‘local clubs were becoming quite excited over the affair’. As usual the entry was dominated by central and west coast clubs. The opening two rounds saw the draw regionalised. The East of Scotland provided 17 clubs, Fife 18, North of Scotland 25, 11 of which were from Dundee, which included Tayport, defined as a Dundee club.
Round 1
Arbroath Dauntless v Tayport
Tayport were drawn away to Arbroath Dauntless on 30th September. Dauntless were reported to ‘have strengthened their forward line considerably and it wouldn’t have been for the want of trying if they didn’t get past the 1st round’.
The tie was at Gayfield and Tayport travelled by the 2.15pm boat to Broughty Ferry then onward to Gayfield for a 3.45pm kick off with the following team –
Coss; Cowley and A.Oswald; Campbell, Cowie and Butters; A.Rae, Wallace, Gray, J.Gray and Wilkie. Reserves were J.Caird, E.Oswald and N.Oswald.
It was good day for ‘Port, returning back over the Tay with a 2-1 win under their belts. According to the Tele, ‘Tayport had all the luck’. But the Arbroath Herald thought that ’the score represents the difference of the teams on play, Tayport being a little the better team’
The town’s interest in the team’s potential for a cup run was building as identified by the Evening Telegraph:

Round 2
Dundee Arnot v Tayport
A visit to Dundee to meet Dundee & District Junior League leaders Dundee Arnot at Stobsmuir on 28 October was Tayport’s 2nd round fate.
Tayport listed Coss; Cowley, A.Oswald; N.Oswald, J.C.Cowie and Campbell; A.Rae, Wallace, Gray, J. Rae and Wilkie. Reserve was C.Caird.
Wilkie had been out with East Fife the previous week and had impressed when the Fifers drew 2-1 with Dundee FC ‘A’ in a Northern League match.
Tayport maintained their good form across the river and progressed to round 3…

Round 3
Norwood v Tayport
Another Dundee opponent for Tayport, this time away to Norwood, bottom of the Dundee & District League. The Coup was the venue on 25th November and Tayport, still defending an unbeaten run for the season, had just won successive cup-ties, left back Oswald netting a hat-trick in a 3-0 win at Crescent in the Telegraph Cup and Rae grabbing the winner in a seven goal thriller at St Andrews City.
Tayport travelled on the 1.35pm train for a 3.35pm kick-off [this was prior to Daylight Saving Time] on The Coup with Coss; Cowley and A.Oswald; N.Oswald, J.C.Cowie and Campbell; A.Rae, Wallace, Gray, J.Rae and Wilkie. Reserves were E.Oswald & C.Caird.
Tayport were fancied to make the last 32 and this was duly achieved by a 3-0 winning margin.
As was often the situation in the 1900s, games were occasionally not completed at the first time of asking. Games abandoned because of darkness, often caused through late arrivals, protests over alleged ineligible players and the inevitable drawn matches, frequently saw ties take three weeks to be completed. There was however a different reason for the Rothesay Victoria v Vale of Glengarnock match to be replayed. The first tie was abandoned after 4 balls had burst during the game and no fifth ball was available!
Surprisingly, very few games were postponed in those days because of inclement weather conditions. Rain, hail or snow and no hot showers, they just got on with it!
Round 4
Dundee Violet v Tayport
Only 4 local clubs now left in the competition, two of which, Violet and Tayport, were drawn together in the 4th round. The tie, on 22nd December at Fairmuir, was the match of the season to date on Tayside.
Tayport had warmed up for the big game by extending their unbeaten run for the season, knocking Carnoustie out of the Courier Cup, the Press describing Tayport ‘playing a rattling good game and entering the second round of the Courier Cup at Carrotopolis’ – a rather quaint label for the Angus town.
Tayport had travelled by boat to Broughty en route to Carnoustie but this week it was the 12.29 train from Tayport for the 2.15 kick-off at Fairmuir.
The Evening Telegraph’s Junicus [my, hasn’t he aged well!] in his match preview, pointed out that ‘there is no doubt that they [Tayport] are going strong and the Dundee team will find in them tough customers and the game should be worth seeing. Tayport have had such a run of success that one is inclined to pin his faith in them although they have yet to meet no mean opponents’
Tayport were unchanged from the Carrotopolis game and fielded Coss; Cowley and A.Oswald; N.Oswald, Cowie and Campbell; A.Rae, Wallace, Gray, J.Rae and J.Wilkie. Reserves – Buttars and E.Oswald.
Dundee Violet selected Laburn; Monteith and Millar; Watson, Leith and Ogilvie; Craigie, Christie, Thomson, Duncan and Hutton.
The Cup progress of the Tayside clubs had not gone unnoticed and it was reported that ‘A Scottish selector is due at the Fairmuir this week to witness the Violet v Tayport tie’
Tayport emerged 3-1 winners and Monday’s Christmas Day edition of the Evening Telegraph commented…

Later in the week, perhaps tongue in cheek, Junicus noted that…

He was only 90 years off the mark!
Junicus continued…

No doubt post-match in 1905 as well as ninety years later, the same brewery’s sales would be given a boost by Tayport’s Scottish Cup exploits!

Round 5
Tayport v Duntocher Hibs
Saturday 27th January
Tayport had reached the last 16, the only cup survivors from north of the Forth, thus going where no Tayport club had gone before.
The full draw was
Arniston Rangers v Kirkintilloch Rob Roy
Burnbank Athletic v Blantyre Victoria
Dunipace v Benburb
Neilston Victoria v Maryhill
Newtongrange Star v Bonnyrigg Rose Athletic
Renfrew Victoria v Darvel
Tayport v Duntocher Hibs
Vale of Garnock Strollers v Kilbirnie Ladeside
Tayport didn’t have the best preparation for their big game, losing 3-2 to St Andrews City in the semi-final of the M’Arthur Cup at Kinness Park the previous Saturday and thus surrendering their unbeaten run for the season. According to a press report (below) the referee was something of a ‘homer’:

Duntocher Hibs from Clydebank had reached the last 16 the hard way, requiring a replay in every round and on two occasions requiring a second replay to progress, but were clear favourites.
5th Round
Tayport 1-1 Duntocher Hibs
The tie, on 27th January was clashing with the match at Dens Park where Dundee, defending a 14-game unbeaten run, were meeting Celtic in the ‘big’ Scottish Cup. It was feared the game at Dens, which would attract a then record attendance of 26,000, would affect the crowds at Junior games. For this reason, all Junior games in the city were off. Both Tayport and Duntocher appealed to the SJFA for an extension of a week to play their tie but were denied the privilege.
The tie went ahead on the East Common on what was certainly a busy weekend in Tayport. The Chancellor of the Exchequer and future Prime Minister Herbert Asquith was in town and attracted a full house in the Volunteer Hall [later the Picture House] for a pre-election speech.
Tayport were again unchanged but despite being urged on by a noisy home support, failed to make home advantage count and true to form Duntocher returned to Clydeside with a replay following a 1-1 draw. Right winger Alex Rae who had been selected for the Scottish Junior FA international trial, was Tayport’s scorer.
Fake News!
It had been reported earlier in the week that Tayport had intended scratching but this was not the case.
So, it was off to Duntocher for the replay on 3rd February, a match which had caught the imagination of the locals.


[Brake – a form of transport carrying 12 – 20 passengers]

5th Round replay
Duntocher Hibs 9-1 Tayport
There are few details of the match but Tayport clearly imploded. A fairly even first half but the heads went down in the second period as Tayport crashed out of the competition.

After a hard-fought draw at home, how the team could lose a replay by such a margin was certainly a talking point back home. There must be a story there, but you’ll have to leave it to your imagination.

….as it transpired, 23 years and Dundee Violet to be exact

Notwithstanding the Duntocher debacle, Tayport’s cup efforts hadn’t gone unnoticed by the Seniors and at the end of the season wingers John Wilkie and Alex Rae had signed for East Fife and Albert Oswald had signed for Dundee.
Exactly 100 years later, in 2006, the Tayport FC of modern times would be back at Duntocher in a Scottish Junior Cup 6th round replay, eliminating Clydebank on penalty kicks before a crowd of 1,202.
Duntocher were drawn at home to Renfrew Victoria, the previous season’s beaten finalists, in the quarter final. It was something of a local derby with the respective grounds only 10 miles apart, separated by the River Clyde. The tie, which had caught the imagination of the locals, ended in a scoreless draw at Hill End Park.

However, controversary and the Scottish Junior Cup were often not too far removed in these days and trouble kicked off in the replay at Renfrew’s Western Park forcing the referee to abandon the game:

continued below…

Renfrew appealed and were awarded the tie but were eliminated in the semi-final by ultimate beaten finalists Kirkintilloch Rob Roy.
1906-1907
227 entries
Round 1 Tayport received a bye
Round 2 Tayport 3 – 4 Dundee Arnot
Arnot had eliminated Forfar Celtic by 3-1 at West Craigie Park, Dundee in round 1.
After the excitement of the previous season the following season was disappointing, to say the least, with Tayport exiting the competition at the first hurdle.
Information regarding this match is pretty sketchy but Alex Rae was back from East Fife and the Tayport line-up was Coss; George and Campbell; N.Oswald, A.Rae and Caird; E.Oswald, Low, J.Rae, Gowans, and Gordon.
Arnot went on to eliminate Forfar West End in round 3 before losing 5-0 to Rockbank in Glasgow in round 4.
Want to be sure to enjoy the Match? Then why not pop into the Dundee Tooth Depot and get that pesky tooth out – 1906 style!!

Round 1
Montrose Rosevale v Tayport
231 clubs had entered this season’s competition with the early rounds being drawn on a regional basis. An Aberdeenshire Region section of the draw had been introduced, but there was also a North of Scotland section which paired Tayport with Montrose Rosevale at Links Park, Montrose in the 1st round on 28 September 1907. Tayport weren’t included in the Fife section which probably confirmed that the high heid yins in Glasgow weren’t exactly sure where Tayport was!
Tayport had always had a goodly number of seafarers amongst its population so it perhaps wasn’t too much of a surprise to learn that the team travelled to Montrose’s Links Park via the North Sea or, as it was called in those days, the German Ocean, by boat. The kick-off was 3.30pm, the boat left Tayport harbour at 12.10pm
Two goals from centre forward Latto gave the ‘Port team a 2-1 win, so there may well have been a few rum-fuelled shanties during the return sail to Tayport harbour and perhaps a nightcap in the Bell Rock Tavern or Freemason’s Arms…or maybe both.
Round 2
Tayport v Arbroath Parkhead
Angus opponents again in Round 2 with Arbroath Parkhead visitors to the East Common on 28th October 1907. Tayport’s star goalkeeper Coss was out through injury but the Arbroath press reported “…his place was well filled by Heggie and although the game was one-sided, this was entirely due to the home side’s persistency and hard work. The big victory of Tayport over Parkhead by 5 v 0 was scarcely looked for and the White and Green brigade will have to pull themselves together”
Tayport had fielded Heggie; Crawford and Lonie; Balfour, N. Oswald and Guthrie; Devlin, A.Rae (capt.), Latto, Campbell and Greig. Reserves were Mills, Irvine and Dorwood.
Round 3
Glenavon v Tayport
For Round 3 on 30th November 1907 it was a short trip to Dundee to meet Glenavon at Fairmuir Park. Tayport fielded Heggie; Crawford and Lonie; Balfour, N.Oswald and Guthrie; Morris, A Rae (capt.), Mills, Campbell and Greig. Reserves were Latto, Irvine, Kay and Henderson. Tayport were never behind, winning 3-2 with goals from Latto, Campbell and Rae.
Round 4
Tayport v Ardeer Thistle
By this stage, the competition was all-in and round 4 favoured Tayport with a home draw v Ayrshire’s Ardeer Thistle.
Some familiar names only a few of which were still going strong in the 21st century:

The rules of the competition decreed that if clubs were more than 100 miles apart, the home club, had to either guarantee the visiting club’s fares or otherwise stage the game at a neutral midway venue – an almost certain loss of money whichever way they decide.
Tayport took the neutral venue option but then agreed to Ardeer’s suggestion that, for a monetary consideration, the neutral venue be in Ayrshire!
Tayport had wanted £15 [worth around £1,850 in 2021] but eventually a deal was struck and they settled for Ardeer’s top offer of £10.
Ardeer’s choice was to play the tie at ‘neutral’ Stevenston, about five miles along the road from Ardeer, on 28th December.
It was noted that…“The Committee of the Ardeer FC have been reluctantly compelled to raise the price of admission to Saturday’s match to 4d. Members on this occaIt was noted that… “The Committee of the Ardeer FC have been reluctantly compelled to raise the price of admission to Saturday’s match to 4d. Members on this occasion are also kindly asked to pay at gate, so as to assist the management in meeting the large expenditure which this important match will entail”sion are also kindly asked to pay at gate, so as to assist the management in meeting the large expenditure which this important match will entail”
The temptation to accept the financial inducement may well have been regretted as the match report records…
“There was a large attendance at Stevenston to witness the encounter between these Fifeshire and Ayrshire teams in the 4th Round of the Scottish Cup. Prompt to time the game started, and in a twinkling Harvie had the ball in the net for Ardeer. The Fifers strove hard to get an equaliser but the Ardeer players were too strong for them and they were repulsed. Another smart piece of play brought a second goal for Ardeer, and at half-time they led by 2-0. On resuming, it was expected that Tayport, with the strong wind in their favour, would make a better show, but this hope was not realised. Ardeer completely outplayed them, scoring four more goals and winning the tie by 6-0”
Tayport‘s line-up was Heggie; Crawford & Lonie; Balfour, Oswald & Guthrie; Morris, Rae, Mills, Campbell & Greig.
The local press also noted…
The visit of the Fifers to the town of explosives was looked forward to with much interest and anxiety by the supporters of Ardeer Thistle. The visitors arrived in Stevenston on Saturday forenoon at 11.30am, leaving Tayport in the morning at 6.12 am. They left Stevenston with the 4.57 pm train for Glasgow where they were to get a connection for home at 8 o’clock. On being asked why they were going away so early from Stevenston, their reply was that “they wanted a wee while in Glesca”. They also remarked that “it was awfu’ cauld doon this way”; and they considered Ardeer ‘grand players’.
1908 – 1909
An eyewatering total of 269 clubs entered this season’s competition.
Round 1
Tayport v Carnoustie Panmure
In previous seasons Tayport had been in the North of Scotland section of the 1st round draw but this season they weren’t one of the 26 clubs in the Fifeshire section but found themselves in the Forfarshire & Perthshire section and a home tie v Carnoustie Panmure on 26th September 1908.
Tayport, relying on much the same squad that reached last season’s 4th round, got off to a promising start in the 1908-09 competition with a 4-0 win over Carnoustie on the East Common.
Round 2
Clepington Athletic v Tayport
The Dundee & District Junior League (D&DJL) was still a closed shop to clubs outwith the city but in cup competitions Tayport often had the measure of their city opponents. However, when drawn away v D&DJL newcomers Clepington Athletic in the 2nd round on 31st October 1908, Junicusinthe Evening Telegraphwas of the opinion that “Tayport will have to show improved form in order to oust Clepington from the Tournament”.
Following a 2-2 draw at North End Park, a prescient Junicus noted that…


Such was the surprise of Tayport’s 6-1 replay win on 7th November 1908 that Junicus later added “Clepington’s defeat at Tayport is unexplainable and is the largest this season”.
Round 3
Tayport v Dundee Harp
on 28th November 1908 paired Tayport with Dundee [Lochee] Harp and again it was another win against the odds, Tayport 3 Harp 2

Junicus had provided a warning…

Tayport’s squad during this season’s cup run was J.Heggie; Sorley, Lonie, Berrie, Cowie, Melville, J.Nicol, Irvine, R.Nicol, N.Oswald, E.Oswald, F.Oswald, Greig, W.Campbell, C.Campbell.
Round 4
Tayport v Mugiemoss
In the 4th round, Tayport, one of only 3 Fife-based clubs left in the draw, were drawn at home to Aberdeen’s Mugiemoss in a Boxing Day 1908 tie on the East Common. It was another tight game but Tayport delighted the home support by edging through by 3-2.
The Aberdeen Press & Journal covered the match:

Round 5
Tayport receive a Bye
To tidy up the draw, there were only two ties in the 5th round, the rest, including Tayport, received a bye into a 6th round, i.e. the last 16. Including Tayport, the draw featured only four clubs from the east coast, the others being Penicuik Juniors, Lochgelly St Patrick’s and Dundee Violet.
As always, the last 16 was dominated by west coast clubs.

Round 6
Yoker Athletic v Tayport
Tayport’s bid to make the quarter finals brought them another trip to Clydeside, this time drawn away to Yoker Athletic on 30th January 1909.

Sadly, the optimism was misguided and “Tayport bade goodbye to the Scottish for another year. The Yoker lads made the most of the first half and Tayport were 4-1 down at the cross-over. With J.Nicol injured, the Fifers did exceedingly well with ten men but were eventually defeated by 6-2”. and later in the week – “The accident to player Nicol of Dundee Tayport [sic] has turned out worse than expected. I understand he has been taken to the Dundee Infirmary this week to go through an operation”
Yoker would go on to reach the semi-final, losing 1-0 to Strathclyde.
1909 – 1910
In season 1909/10 Tayport didn’t enter the Scottish Junior Cup