The following season saw the Town clinch the FAI Intermediate Cup which was a considerable achievement coming so soon after promotion from the Junior ranks.

[citation needed] The appointment of the then 26-year-old rookie manager Stephen Kenny in the summer of 1998 proved the catalyst for a major upturn in the club's fortunes on the pitch.

[citation needed] Longford performed admirably in their first season back in the Premier Division finishing in mid-table.

As Bohemians had also won the league title that season, Longford qualified to play in the UEFA Cup in July 2001.

[8] Things were less comfortable in the league during the 2001/02 season after that, as they ended up in the relegation/promotion play-off, where they played Finn Harps in a two-legged affair.

After the 2002/03 season, the club became an established top division side, led by manager Alan Mathews, with four successive top-six finishes.

[citation needed] In October 2003, the Town clinched their first title in senior football when winning the FAI Cup following a 2–0 victory over St. Patrick's Athletic at Lansdowne Road.

[9] The winning Longford side Stephen O'Brien, Alan Murphy, Barry Ferguson (captain), Brian McGovern, Seán Dillon, Alan Kirby, Vinny Perth, Philip Keogh, Sean Prunty, Shane Barrett and Sean Francis – with Barrett and Francis as goal-scorers.

Trailing with five minutes to go, late goals by Waterford-born Alan Kirby and sub Paul Keegan meant a "sensational finish" for Longford Town.

[12] The 2007 season was a disappointing one for the club as, along with losing the FAI Cup final to Cork City, the team were relegated after finishing bottom of the Premier Division.

That does not tell the whole story however,[tone] as Longford were deducted six league points during the season for failing to comply with club licensing procedures.

The title was clinched, under the management of Tony Cousins, following a resounding 5–0 victory at home to Shamrock Rovers B on 3 October 2014.

[21] Last update: July 2005[22] Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.