Season 1910/11
Tayport, now playing in the Inter County Junior League based in Dundee and entered in an assortment of cup competitions on both banks of the Tay had, after a year’s Scottish Cup hiatus, again entered the competition. There was an entry of 248 clubs, 21 of which were from Forfarshire [Dundee and round about] and 31 from Fife. The SJFA had decided that, for this season’s competition, Tayport would be classed as a Fife club.
Round 1
24th September 1910
Tayport v Balgonie Scotia

Tayport – Anderson; Wilkie & Guthrie; Pearson, A. Rae & D.Rae; Connolly, Oswald, Henderson, Walker, Y.Rae.
Round 2
29th October 1910
Tayport 4 Cupar Athletic 2
Unfortunately, there are no details of this win which put Tayport into the 3rd round. Sadly, Tayport were without their regular right back James Wilkie who had succumbed to an illness and died earlier in the month.
Round 3
26th November 1910
Tayport 1 Loanhead Mayfower 1
The Midlothian press reported that Loanhead were“undertaking a long journey to Tayport but have exceedingly high hopes as to the ultimate issue of the tie. Tayport are to us an unknown quantity but the experience of the Loanhead eleven will probably carry them to victory”m to victory”

3rd December 1910
replay
Loanhead Mayflower 3 Tayport 3
The replay preview in the Midlothian press predicted that ”Loanhead seem certainties…Loanhead got a fright at Tayport and it was only in the closing minutes that their equaliser was secured”


10th December 1910
second replay
Tayport 1 Loanhead Mayflower 2 (aet 90 mins 1-1)

Tayport’s line up for the Loanhead tie was – Grieve, A.Rae & D.Rae; Pearson, Anderson & Guthrie; Niven, Connolly, Henderson, Oswald & Y.Rae.
Such was the profile of the Scottish Junior Cup in those days, that if you were in Hong Kong and picked up a copy of the Overland China Mail in July 1910, you would have read that “As a result of a protest, the Final of the Scottish Juniors’ Cup had to be replayed and Ashfield were again winners against Kilwinning Rangers. And there is the likelihood of another protest”
1911-1912
Again, there was confusion as to which Association Tayport should belong but on application by the club, no doubt for logistical reasons, the East Region of the Junior FA (ie Fife and Lothians area) agreed that Tayport should be allowed to join the Forfarshire JFA. However, when the SJFA made the draw for the 1st round of the Scottish Junior Cup, Tayport found themselves in the Fife section of the draw, at home to Lumphinnans Swifts.
Saturday 30th September 1911
Round 1
Tayport 1 Lumphinnans Swifts 1
Tayport fielded Coss; A.Rae and Gallacher; Anderson, N.Oswald & Kidd; Croll, Connolly, E.Oswald, Rae and Pryde. The sides drew 1-1 on East Common with Norman Oswald netting the home goal.
For whatever reason, rather than travel to Lumphinnans for the replay, Tayport decided to scratch from the competition.
Fairfield FC, the leading Dundee Junior club at the time, was going well in the national competition and in the 5th round accounted for Irvine Meadow XI at Tannadice by 3-0 but were eliminated by beaten semi-finalists Cambuslang Rangers.
1912 – 13
21 September 1912
Round 1
Tayport 1 Crossgates Thistle 1
Tayport FC was again in a position which would be repeated regularly over the next 100 years i.e. Fife or Forfarshire? In August it was reported that at a meeting of the Forfarshire Junior FA, “Tayport wished to be drawn with Forfarshire in Scottish ties but Forfarshire could not see their way to granting this request”.
There were 234 entries for the competition, including 16 clubs from Fife amongst which were Tayport and other local north Fife sides St Andrews City, Newburgh West End and Cupar Violet.
In the regionalised round 1 Tayport were drawn at home to Crossgates Thistle. The West Fife press reported that “Thistle have the longest journey – to Tayport – but the Jags don’t anticipate trouble from the journey”.
The teams drew 1-1 but Tayport clearly must have anticipated trouble from the journey as, for a second successive season, they scratched from the competition rather than replay.
Tayport’s player pool was Coss; A. Rae, Gallacher, Anderson, N.Oswald, Niven, Turnbull, T.Rae, Connolly, Pryde, F.Oswald, Main, Wilkie and J.Rae.
1913 – 14
27th September 1913
Round 1
Tayport 1 Lumphinnans Swifts 0
It was familiar west Fife opponents this season with a 1st round tie v Lumphinnans Swifts, now members of the newly founded Fifeshire Junior League. Lumphinnans were fancied but they clearly missed their crack centre forward Harry Lister who had just signed for Dunfermline Athletic and Tayport went through by the only goal of the game.
Tayport had lined up McKay; Rae and Guthrie; J.Anderson, F. Anderson and J.Henderson; Oswald, Christie, Parnell, Campbell and Latto.
Tayport were one of 9 Fife clubs remaining in the Cup and as it was still a regionalised draw, reached the 3rd round by way of a bye.
Round 2
a bye
Round 3
8 November 1913
Arniston Rangers 3 Tayport 1
The draw for round 3 saw Tayport visit Gorebridge for a tie v Arniston Rangers. Musselburgh News reported:-

The local reporter wasn’t wrong and Tayport made their exit from the competition. No disgrace but they found Arniston “in good fettle and full value for their 3-1 victory”
It would be exactly 85 years before a Tayport team would again visit Gorebridge for a Scottish Cup tie. That was 1998 and they exacted some revenge, winning 4-1 win against Arniston on a snow covered Newbyres Park

1914 – 1915
The start of the season coincided with the start of the Great War and life for people living in those times would be changed for ever. Football was no exception

September 1914
Round 1
Cupar Violet v Tayport
The 1st round draw paired Tayport with Cupar Violet in Cupar but the tie never went ahead as Cupar scratched from the competition
Round 2
Glencraig Celtic 3 Tayport 0
Tayport made their exit from the competition in the heart of Fife’s coal mining community, losing 3-0 to Glencraig Celtic.
Although the Scottish Junior Cup continued to be contested during wartime, competitive football in Tayport virtually closed down during the War with many of the young men of the town signing up for the war service or merchant service with the result that Tayport didn’t enter the competition again until the 1919/1920 season.