The first record found regarding Llanfair Caereinion Football Club was that of a football dinner report in 1896 which outlined that the club had played 9 games, winning 5, drawing 2 and losing 2.

Then, on Wednesday September 23rd, 1896 a meeting was held to form Llanfair Football club as a league team. Although it was agreed that Llanfair should enter a league team, they only played friendlies for a few more years and didn’t actually play their first Welshpool and District game until 18th November 1905 when they beat Powis Castle. On 13th February 1897, a match report details a game between Llanfair and the Welshpool Excelsiors. Despite having only 10 men for the whole game, Llanfair won 13-0. There is an early photo from 1906 with a few special sub plots to the story. Of the 11 players who played that day, 10 had the surname Astley and Ifan Astley, who played, was offered first team terms with Everton but turned them down.

In the late 1930’s, just before the war, Llanfair narrowly missed out on the Montgomeryshire league title in 1937 when they lost in a play-off against Caersws. They were also runners up a year later in 1938, again to Caersws.

After the Second World War, Llanfair Caereinion started up again and became a flourishing side. During the late 1940’s they won their first league title, the Montgomeryshire Amateur League in both 1947 and 1948 and finished runners up in 1949. In 1950 they continued their successful spell by winning the Montgomeryshire Amateur League Cup. Also, during the 1940’s, a centre half by the name of Trefor Owen made a name for himself by captaining the Welsh Youth team whilst playing for Llanfair Caereinion. He went on to earn 6 Youth caps and 18 Amateur International caps and he also ended up playing for Leyton Orient in the 1960’s.

Throughout the 1950’s and 1960’s, it was a case of being the ‘nearly men’, finishing runners-up in the league on three occasions in ’51, ’54 and ’63. In 1952/53, Llanfair played in the Welsh Cup for the first time, losing 6-0 to Newtown. They also lost in the final of the Montgomeryshire Cup in 1951, losing 3-1 to Welshpool.

Interestingly, in 1962-1963, the league was scrapped due to the delay caused by severe floods. As it would not be possible to complete all matches, the League was divided into four zones, the winners of each group then played a semi-final and final. Llanfair won their group and beat Newtown Arms 3-2 in the semi-final. Unfortunately, though, they lost in the final to Forden, 2-0.

In 1966, another Llanfair Caereinion player represented his country and signed professional papers. Fifteen-year-old Kingsley Whiffen, a goalkeeper at Llanfair since the age of 13, was spotted playing for Montgomeryshire Schoolboys and was asked to sign as an apprentice professional for First Division club Chelsea FC, after only one trial game for their youth team. Whiffen was spotted by local scout Stan Berry who also spotted Trefor Owen. Earlier that year, Whiffen represented Wales Schoolboys at Wrexham against Scotland.

In 1969, Llanfair were relegated to Division 2 but immediately came back up again. After finishing league runners up in 1971 and Amateur League Cup winners in 1972, Llanfair pulled off a magnificent treble in 1972/1973. Firstly, they won the Montgomeryshire Amateur League First Division for the first time in 25 years. They then won the Montgomeryshire Village Cup by beating Llanfechain 2-1 before beating Llanfyllin 3-2 to win the

Amateur League Cup. They went on to win the league again in 1975 and were promoted into the Mid Wales League, where they stayed and competed well for the next 5 years. In 1980 though, through choice, they returned to the Montgomeryshire Amateur League.

When Llanfair joined the Mid Wales League in 1975, they formed a Reserve side that competed in the Amateur league until 1980. They also had a successful few years winning Division 2 in 1979 and probably most notably, they won the popular J.Emrys Morgan Cup in 1978, beating Tregaron 2-1 in the final after a replay. Also, in a sign of things to come, Llanfair Youths won the Mid Wales Youth Cup in 1979.

Like the 70’s, the 1980’s was a very successful time for Llanfair Caereinion Football Club. In 1984, they won the Emrys Morgan Cup for the second time, beating Builth Wells in the final. In 1985 and 1986 they won back to back Montgomeryshire League titles and in 1986 they won the Emrys Morgan Cup again, this time beating Llanfyllin after a replay. Llanfair then did another back to back win when they lifted the Montgomeryshire League trophy in 1989 and 1990 taking the clubs total to 8 Amateur League Titles.

In the nineties, they came so close to continuing their success but finished runners up in the league in 1991, 1992 and 1993. However, they were successful in cup competitions. In 1990 and 1993 they won the Town Cup having taken part in the Village Cup in previous years. In 1991 they won the Amateur League Cup along with a record 4th Emrys Morgan Cup win, which Llanfair still proudly hold the record of today. They defeated Vale of Arrow in the final.

The 1993 Town Cup was a special one for the Town as it was played between two Llanfair teams. In 1989/1990, Llanfair Wanderers formed as a club so that a fresh batch of youngsters could play Amateur League football. In only their second season they finished second in Division 2 on goal difference and then played in Division 1 alongside ‘Llanfair Caereinion’ until 1996 when they were relegated back into the 2nd Division. The 1993 final was won 3-0 by Llanfair Caereinion.

The late 1990’s was a barren spell for Llanfair with neither side winning any notable silverware. In 1998, Llanfair Caereinion actually finished bottom of Division 1 with only 9 points but somehow avoided relegation.

In the 2001/2002 season, Llanfair United FC was created when both Llanfair Caereinon and Llanfair Wanderers merged to form one side. In their first season they finished a very respectable 3rd and won the Tanners Town Cup for the 3rd time in the town’s history. In 2004, Llanfair United Reserves were formed.

In the 2010/2011 season, the club took the decision of joining the newly formed Spar Mid Wales Division 2. It was the first time the club had played in the Mid Wales League set up since 1980, 31 years ago. In their first season, they finished a valiant 6th place. After going 10 years without winning a trophy, it was the Reserves who gained the next piece of silverware. After finishing predominantly near the bottom of Division 2 since their creation, the Reserves went from 2nd bottom in 2011 to being champions in 2012. Also in 2012, the first team narrowly missed out on promotion to the 1st Division by 1 point but did win the ER Jenkins Division 2 Cup. Not disheartened by their narrow failure, they went on to win Division 2 in 2013 having only lost one game and retained the ER Jenkins cup by beating Machynlleth after extra time in a thrilling cup final.

In the 2012/2013 season, Llanfair United formed a Ladies team for the first time in their history. They were previously known as Meifod Ladies but made the switch to be part of the town’s footballing community. In the same season, Llanfair once again started a Youth team.

The 2013/2014 season will go down as one of the best in the club's history. The club ended the season with 5 trophies which included the Central Wales Cup (First Team), Montgomeryshire Amateur League (Reserves), North Powys Ladies League and League Cup (Ladies) and the Mid Wales Youth League (Youths). In the Central Wales Cup final, Llanfair defeated Berriew 2-0 at Latham Park, watched by a bumper crowd from the town.

The 2014/2015 season proved to be very historic indeed. Llanfair Football Club were crowned Spar Mid Wales League champions for the first time in the club's history and went on to win the Montgomeryshire Cup for the first time with a 2-0 win over Carno in the final. Along the way, the first team also narrowly lost 3-2 to Caersws AET in the Central Wales cup and lost in the semi-final of the Spar League Cup. The Youths also won the league, retaining their title whilst the Ladies and Reserves finished 3rd and 5th respectively.

In 2015/16, the Reserves managed to win the prestigious Emrys Morgan Cup for a fifth time for the club. They won 2-0 against Llandysul in a thrilling final at Penrhyncoch. Toby Evans getting both of the goals in the 44th and 93rd minute. Chris Humphreys made an important penalty save in the 91st minute at 1-0 in a tense and dramatic final. The Reserves also went on to win the league title. The first team found their first season in the Cymru Alliance difficult and ended the season in 15th place but avoided relegation. They went on to win the Montgomeryshire Cup though for the second time by beating Carno 3-1 in the final. James Davies, Matt Spencer and Paul Griffiths got the goals. The Ladies finished 6th in their league and runners up in the Central Wales Cup whilst the Youths lost in their league semi-final play off.

In 2016/17, the first team continued their Huws Gray Alliance adventure, but it unfortunately came to an end being relegated even though the club finished 13th (4th from bottom). The club reached the quarter finals of the Welsh Cup after a memorable cup run, beating Welsh premier side Cefn Druids along the way before losing to Caernarfon. The first team finished on a high though winning the Montgomeryshire Cup for the third time in a row, with a 3-1 win over Llanrhaeadr at Llanfyllin. Goals from James Davies(2) and Andrew Hughes sealed the win. The Youth team had a memorable season, winning all three trophies at their disposal. They won the league with a 4-0 win over Caersws. They had already by that time won the League Cup with a 3-1 over Welshpool and the Central Wales Youth Cup with a 4-1 win over Caersws. The Ladies had a good season too, finishing 2nd in the league but narrowly losing out in the Central Wales Cup final to Aberystwyth, 2-1 and in the semi-final of the league cup. The Reserves finished 8th and runners-up in the League Cup after losing 3-1 in the final to Caersws.

The 2017/18 season was a quiet one on the trophy front. The first team finished a very respectable 4th whilst the Ladies finished brilliantly in 2nd place. The Reserves finished 5th whilst the Youths didn’t make the play-offs to challenge for the title.

In 2018/19, the first team won their 2nd Mid Wales League Championship after a gruelling season against a number of top opponents. They sealed t on the last day of the season in dramatic fashion at Kerry. The Ladies also had a brilliant season, completing an amazing treble. They shared the league title with Bethel whilst beating their title rivals twice to win the NEWFA Cup and the North Wales League Cup. The Reserves finished 7th whilst the youth team failed to make the play-offs.

The 2019/20 season was rocked by the Coronavirus pandemic and the season was ended early. There had been enough games played for Llanfair to compete in the newly formed Cymru North which replaced the Cymru Alliance. However, it proved to be a challenging season and Llanfair finished bottom on points per game. The Ladies won their league on points per game whilst the reserves and youths barely played.