The onset of the 20th Century saw football become more structured and in 1903 The Clogher Valley League was organised; only accepting entries from teams based within five miles of the Clogher Valley Railway Company’s line. Competing teams included Maguiresbridge Lilywhites, their village rivals Maguiresbridge Deadshots, Fivemiletown, Aughnacloy and Caledon. A trophy was donated by the directors of the Railway Company.

The 1903 the Impartial Reporter recorded the Fivemiletown team which drew with Aughnacloy in the League as “Goal – Chiddick; backs, P Roche and F Roche (capt); halves , McLoughlin, Carruth and Armstrong; forwards, McNulty, Curruth, Sloan, Gillespie, Martin”.

The early days were not without controversy. A Fivemiletown official wrote a letter to the Impartial Reporter in the same year to express some concerns

To the editor of the Impartial Reporter:-

"Sir – In connection with the competition for the Clogher Valley Cup, a match was played in Aughnacloy between Caledon F Club and Fivemiletown. The weather being unfavourable, play was not as good as anticipated. From the very start of the game it was evident that Fivemiletown team would get a rough evening. The spectators were in favour of Caledon. During the entire time they interfered with the players not only by using abusive language but by actually threatening the players. The goalkeeper was about to get beaten by them only for the interference of two of the Royal Irish Constabulary, who protected him during the remainder of match. Such conduct should not be tolerated on a football field; it has tendency to lessen the sport of the game.

I think the Clogher Valley Railway Company should offer some protection to players, and appoint a competent referee whose decisions cannot be waved by the spectators, nor let the ball be kicked in from touch by the spectators and played on. He should also not allow one player to kick another behind, nor allow one of the Caledon players to go about shaking his fist in a player’s face and want him to fight. This was a usual occurrence and does not tend to further the football game on the Clogher Valley Company"

Yours W Gillespie

The editor of the Impartial added a footnote stating “As this matter needs some attention, and as the letter is written by a prominent football official, we publish it. The referee may not have been to blame; he may have done his best. But it is well to ventilate the matter in the public interest”

Caledon went on to win the Clogher Valley League that year! Fivemiletown do not appear to have finished the season!

As the popularity of football grew the newly formed Fermanagh and South Tyrone Football Association met in Enniskillen in 1904 to consider entries and arrange fixtures for a new league. The teams that competed in that inaugural season were Moonlighters, Celtic, Enniskillen United, Enniskillen Corinthians, Fusiliers, Lisbellaw, Tempo Freebooters, Derrygonnelly, Omagh United, Fintona and Fivemiletown. Enniskillen won the league that season finishing ahead of their local rivals, Corinthians. In 1907 the football association was renamed The Fermanagh and Western District Association.

From that team, O’Malley and B Boyd were selected to play for a Fermanagh & Western team against the Amateur League (Belfast). The Belfast side came out 5-2 winners.

More Silverware followed with Fivemiletown teams winning the Coffey Cup in 1939 and 1941. Also in 1941 the Mulhern Cup was won again, this time on the field of play with the team defeating an Army XI 4-2.

The Impartial Report on June 5th 1941 recorded the satisfaction felt about the Mulhern Cup success:

“Fivemiletown Football Club realized a cherished ambition on Friday evening when they won the Mulhern Cup, a distinction that had eluded them for a number of years. The duties of secretary of the Club for some years past have been ably carried out by Mr. Thomas N Morrison, who has installed wonderful enthusiasm into the team and despite limitations in its size, this Clogher Valley town always has been able to field a team of worthy cup fighters. Fivemiletown’s opponents in the cup final on Friday evening were an Army XI, the match was played on the Broadmeadow, Enniskillen before a large attendance.
 
The Clogher Valley town fielded a strong side; captained Johnny Breadon and their opponents included many experienced players. The Army side however were unable to withstand the dash and determination of the Fivemiletown team who ran out winners by two goals to nil. The first half was scoreless, but midway through the second half the large crowd of Fivemiletown supporters were able to give vent to their feelings when Tommy Breadon, brother of the Fivemiletown captain scored for the Clogher Valley team. About 10 minutes afterwards Fivemiletown’s outside right put the game beyond doubt when he scored the second goal to leave Fivemiletown winners by two goals to nil. More goals would undoubtedly have been scored but for the outstanding display by both goalkeepers. At the conclusion of the game there were wild scenes of enthusiasm when the Fivemiletown players were carried shoulder high of the field.

Congratulatory speeches were made and Mr John Breadon expressed his pleasure at captaining the successful team.”

In 1946 a Fivemiletown United team is recorded as newcomers to the league – the first mention of the United name. However the league in question is the Clogher Valley League and the sport is table tennis!
 
On August 21st 1947 a match is recorded as having taken place between Augher Stars and Fivemiletown United in the Lisnaskea and District Summer Football League. From the research conducted for this history this has been the earliest mention found of a Fivemiletown United FC. Fivemiletown won the match 3-0.
 
During this decade there appears to be several different Fivemiletown football teams playing under different names. In the Mercer and Mulhern Cup’s that year (1947) a Fivemiletown FC and a Fivemiletown Athletic Club both competed against each other. However over the next few years the Fivemiletown United name became the dominant name for football in the town and references to the likes of Fivemiletown Athletic fade away.