St Patrick's Athletic and Bohemians are the only current League of Ireland clubs never to have been relegated from the Premier Division.

Brian Kerr guided the club to success in 1989–90 and 1995–96 before Pat Dolan and Liam Buckley added further titles in 1997–98 and 1998–99.

[3][4] The 1992–93 season saw Cork City win their first title in dramatic circumstances after a series of three-way play-offs that also involved Bohemians and Shelbourne.

[7][8] The first live league game was broadcast on RTÉ2 from Tolka Park between Shels and Derry City during the 1996/97 season.

They were only declared champions after St Patrick's Athletic were deducted 15 points for fielding Charles Livingstone Mbabazi while he was ineligible.

[10] During the second half of the decade a number of Premier Division clubs suffered financial difficulties.

During the 2005 season Shamrock Rovers entered into examinership and it was revealed that the club had debts of nearly €3 million.

This ultimately resulted in the club being relegated to the First Division after they lost the relegation/promotion playoff to Dublin City.

[11][12] During the 2006 season the Revenue Commissioners took High Court action and threatened to have Shelbourne wound up after the club failed to pay more than €104,000 in outstanding taxes.

Despite winning the title Shelbourne were subsequently demoted to the First Division due to their financial difficulties.

[15] During the 2008 season both Cork City and Drogheda United were deducted ten points after going into administration.

Derry City were accused of making extra payments to players using unofficial secondary contracts.

This was against league rules which placed limits on the amount clubs could spend on players' wages.

Cork City had been in serious financial difficulties for several seasons and its holding company was eventually wound up by the High Court.

This period was led by Dundalk and Cork City, taking both the top spots in the league and the definition of the FAI Cup between 2014 and 2018.

In 2011,Shamrock Rovers became the first team in League of Ireland history to reach the group stages and Dundalk repeated the feat in 2016 and 2020.

However, the costs associated with professional football and the pursuit of European success have been blamed for the financial difficulties suffered by Premier Division clubs.

During the course of a season (from February to November) each club plays the others four times (a quadruple round-robin system), twice at their home stadium and twice at that of their opponents, for 36 games.

[40] The report also showed that LOI attendance rose 20% between 2022 and 2023, among the highest percentage increase in crowd sizes in top tier European leagues.