Contemporary records of organised association football in the Dundalk area between the late 1880s (when the game was introduced), and the end of the World War I, are incomplete.

[6] They adopted the name "Dundalk Rovers" for the step up, but they did not survive the season, being requested to resign from the League "owing to their inability to fulfil their engagements".

[11] The following season it led the foundation of the Dundalk and District League (DDL) alongside Drogheda, St. Nicholas's, St Mary's College, Carrickmacross, and the Great Northern Railway.

The League appears to have been inactive for the seasons 1909–10 to 1912–13,[13] at a time when Gaelic football had become the dominant sport in the county (with Louth qualifying for three All-Ireland Finals in those years).

[14] Rovers were replaced by St Nicholas's as Dundalk's representatives in the Irish and Leinster Junior Cup competitions in those seasons.

At first, they played challenge matches against other teams in the area, including sides from British Army regiments garrisoned in the town, then became founder members of the DDL in 1905–06.

split with the Belfast-based IFA), a new Free State League was formed for the 1921–22 season, made up exclusively of Dublin-based sides.

and under the management of Joe McCleery (ex-Belfast Celtic), travelled to Cork to face fellow works-team Fordsons in the opening match of the 1926–27 season.

The result was a 2–1 defeat for the new boys in a match the Cork Examiner described as being "one of the best ever seen in Ballinlough",[33] Joey Quinn (one of three veterans remaining from the junior football days) with Dundalk's first League of Ireland goal.

Proof that they could compete at a national level gave the management committee confidence to press ahead, and the club was converted to a membership-based company— "Dundalk A.F.C.

[42] Following on from the City cup win, they led the Shield midway through its schedule, but, despite only losing once, they fell away due to the number of matches drawn.

There was a similar story in the League, where they had the best defensive record and thrashed eventual champions Shamrock Rovers 5–1 in Glenmalure Park,[45] but a run of three defeats saw them fall two points short of the title.

The following September, in the new season, a second Dublin City Cup was added, with victory over Drumcondra in the final,[53] but they couldn't keep up the momentum and missed out on forcing play-offs by a single point in both the Shield and the League.

So the committee decided to invest its surplus from transfer dealings that season on a player-coach (Ned Weir), and a number of full-time players, in an ambitious attempt to win the trophies that had been beyond reach.

[59] But the new team fell short in both the Shield and the League, and, despite the Cup double and improved gate receipts, the additional income was not enough to cover the increase in costs.

Player sales tailed off after his departure, and the subsequent drop in income left the club struggling to make ends meet.

[68] Inside-right Hughie Gannon broke his jaw in the process of scoring the only goal of the final and missed the celebrations, having to spend a week in hospital.

The club's highest finish in 12 seasons lead to optimism that the lean years might be coming to an end, and, to help make the case, a second Leinster Senior Cup was picked up in 1960–61.

[83] Employment at the works dwindled over the subsequent years and the company eventually went into receivership in 1985 with the loss of the remaining 300 jobs - at a time when unemployment in the town had reached 26%.

[52] The competition survived until the end of the decade, but a combination of factors (the failure to resolve the split, the withdrawal of Belfast Celtic from the Irish League, and the entrenchment of sectarianism in the Northern game) saw it discontinued.

[91] Dundalk had finished as runners-up in the League in 1947–48, unbeaten at home, and with a healthy surplus from improved gates, friendlies against Everton and Luton Town, and transfer dealings.

As things stood, gate-receipts did not match wages, and player transfers to England in the years following World War II were keeping it afloat.

[94] Prole was a Great Northern Railway employee from Dublin[95] who joined up to fight in World War I, before moving to Dundalk to the G.N.R.

For instance, he was calling for a close season for the League in winter and playing into the summer as early as 1937,[99] and was critical of RTÉ in FAI meetings in 1965 for scrapping its soccer highlights show and the broadcaster's lack of publicity for its replacement.

Sam Prole vacated the role of Chairman of the FAI Council the same summer, bringing his 50-year career as a football administrator to a close.

Despite starting out as a full-back, he scored 16 goals in 20 games when pressed into service at centre-forward in his debut season, including a hat-trick in his first match in the position.

His first cap came aged just 19 in a defeat to the Netherlands in December 1935 (a game that also featured Dundalk's Joey Donnelly), after which 'Socaro' of the Irish Press wrote: "The score at the end was 5–3 - but for that small margin thanks, in the most lavish terms, are due to O'Neill, our right full back... [He] was brilliant.

A 1–1 draw away to Germany was his 11th and last cap in Ireland's final match before the war, a game that saw two Dundalk full-backs play (the other being Mick Hoy).

[112] One of Jim McLaughlin's first tasks at Dundalk, after being appointed player-manager, was to play in a Dundalk-Drogheda selection for the Jimmy Hasty benefit match in Oriel Park on 13 December 1974.

He was also the joint top-scorer in the 1963–64 season and had assisted the first goal and scored the second in the famous match in Zurich - the first away victory by an Irish side in European competition.