[3] The poor form continued into the league, and manager Martin Murray resigned at the end of September, less than six months after the cup final victory.

Under Ian Foster, they won the first European match played in Oriel Park since 1991,[18] and lead the league table midway through the 2010 season.

[19] Foster's contract expired and he was allowed to leave, and they spent the 2012 season rooted in the relegation play-off spot, as the scale of the financial problems threatened to put the club of business altogether.

Matthews put the club up for sale,[21] and, with the assistance of a Supporters Trust, it was taken over by local businessmen Andy Connolly and Paul Brown (owners of the team's official sponsors, Fastfix).

[27] Kenny kept the nucleus of the side together and made some more additions for the following season and Dundalk went on a charge to the top of the table, including dishing out a thrashing to defending champions St. Patrick's Athletic in Richmond Park.

The 2015 season saw them dominate, winning the club's third League and FAI Cup Double,[31] losing only one match in the process, three years after the financial and ownership issues that had threatened its existence.

A third league title in a row was sealed with two games to spare in 2016,[32] and Kenny's team made history the same season by being the first Irish side to gain a point,[33] and then to win a match, in the group stage of European competition.

However the club's European form had attracted interest from abroad, and a consortium of American investors, backed by sports-investors Peak6, completed a takeover in January 2018.

[38][39] In the aftermath, the FAI moved to offer Kenny the Republic of Ireland U-21 manager's role, and he resigned at the end of November in order to accept the position.

In the FAI Cup, which also had a schedule change as a result of the pandemic, they reached the final after wins over Waterford, Cobh Ramblers, Bohemians, and Athlone Town.

[63] The 2021 season saw Shane Keegan named first-team manager with Giovagnoli reverting to the position of 'coach' because the latter had been unable to secure a place on a UEFA Pro Licence course.

[64] The season began with a victory in the President's Cup,[65] but after a run of defeats at the start of the league campaign, both Keegan and Giovagnoli left the club.

[66] After a period where new Sporting Director Jim Magilton took charge, Vinny Perth returned to the club as head coach in June.

[68] Before the season ended, the club was returned to local ownership when a consortium led by former co-owner Andy Connolly and sports technology firm STATSports agreed a takeover with Peak6.

[71] They failed to capitalise in the 2023 season, exiting the Conference League in the second qualifying round and finishing mid-table and outside the European qualification places.

[72] The club's finances were quickly deteriorating and there was another change of ownership in the close season, when it was taken over by a US-based Irish businessman, Brian Ainscough.

He was replaced on an interim basis by the club's Head of Football operations, Brian Gartland, and first team coach, Liam Burns.

[80][81] Ainscough passed control of the holding company to a Dundalk-based barrister, John Temple, which avoided a mid-season withdrawal from the league.

[86][87] That results from 2002 and 2003 could be used to deny the club promotion to the 2007 Premier Division infuriated many Dundalk supporters and proved to be the final straw for one particularly disgruntled fan, who entered the former headquarters of the Football Association of Ireland at Merrion Square, doused the reception area with petrol and threatened to set it alight.

[88] Dundalk's owner, Gerry Matthews, met with the FAI and members of the IAG committee and subsequently acknowledged that the club were "happy to move on".

In May 2009 defender Dave Rogers was sacked by the board for dropping his shorts in front of visiting St Patrick's Athletic fans in Oriel Park which resulted in being sent off.

[92] Less than a year later the club was again forced to pay out following another unfair dismissal case, with a former marketing manager winning €40,000 at an Employment Appeals Tribunal.

[93] In July 2010 Neale Fenn, who had been signed from Bohemians at the start of the season,[94] approached the club and requested that his contract be cancelled as he wished to retire from the game "for the good of his family".

[82] Following Temple's efforts to get the debt situation under control, thus avoiding examinership, the club was belatedly awarded a licence to compete in the 2025 League of Ireland First Division.