In October 1975 an immaculately dressed Italian stepped off a bus into a muddy field in the Irish midlands. The Italian was recently retired footballer Giovanni Trapattoni who, having twice won the European Cup with AC Milan as a player, had recently begun his coaching career.
Trapattoni was making his way into St Mel’s Park, where a record attendance of 10,000 had squeezed in to watch Athlone Town’s first adventure in European football continue as they hosted Milan in the second round of the Uefa Cup. Treading carefully across the puddles Trapattoni could scarcely have imagined that his then nascent managerial career would end 40 years later with him returning to Ireland to manage the national side for five years.
What was clear even then was the visitors’ dissatisfaction with the facilities on offer, as they chose to travel with their own chef and supply of wine. An advance party sent to sort out logistics made it clear that Milan would not be training at St Mel’s Park – and they were shocked to be informed that that was correct, because they would actually be playing there.
Years later Athlone Town squad member Eugene Davis told RTÉ: “I actually saw them stepping out of the bus. I saw all these guys getting off in their lovely Armani suits and shoes, then stepping off into puddles of water before they came over to the dressingroom.”
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The first leg finished 0-0, with Athlone blowing a glorious chance to secure the greatest shock result in the history of European club competition when John Minnock had a penalty saved.
In the return the stalemate continued for well over an hour before Milan rallied to win 3-0 in front of nearly 50,000 spectators. At the end of the tie the Athlone players were surprised by the reluctance of Milan players to swap jerseys, until they realised that their black and blue striped kit were also the colours of city rivals Inter Milan.
Almost exactly half a century later the Irish public will finally get another chance to watch Milan on Saturday when they visit the more salubrious Aviva Stadium to play Leeds United in a preseason friendly. Milan did play a competitive fixture in Ireland in September 2020, beating Shamrock Rovers 2-0 in the Europa League at Tallaght Stadium but that game was played behind closed doors because of the Covid-19 pandemic.
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A number of the Milan squad have happy recent memories of the Aviva, most notably goalkeeper Mike Maignan whose last-minute wonder save from Nathan Collins’s header in March 2023 enabled France to cling on for a 1-0 win over Ireland in a Euro 2024 qualifier. Maignan was recently announced as the captain of Milan for the 2025-26 season, becoming the first non-Italian to hold the role since 1961.
In 1948 Paddy Sloan became the first Irishman to appear in Serie A when he moved from Sheffield United to Milan for £10,000. Sloan scored nine goals in 30 games in his single season at Milan, enabling them to finish second behind a dominant Torino side winning its fifth consecutive championship. Months later that all-conquering “Il Grande Torino” team would be wiped out in the Superga air disaster as they travelled back from a friendly game against Benfica.
In the aftermath of the tragedy Sloan briefly joined Torino. Despite his success there, it was well over 70 years before Milan bought another Irish player. In January 2022 Cathal Heffernan moved there from Cork City. But despite regularly playing age-group football he was unable to break into their first team and moved on to Newcastle United in 2023.
A couple of other Boys in Green nearly ended up at the San Siro. In 2023 Milan reportedly bid £15 million for Andrew Omobamidele. More surprisingly, in 2020 Jeff Hendrick was linked with a move to AC Milan, with the Irish midfielder observing with admirable understatement that the transfer speculation “gave me a bit of a confidence boost, I have to say”.
Milan have been crowned champions of Europe seven times, placing them second in the all-time roll of honour behind 15-time winners Real Madrid. Despite this they have only ever played competitively against Leeds United three times, beating them 1-0 in the 1973 Uefa Cup Winners’ Cup Final.
The most recent meetings came at the group stage of the Champions League in 2000, when a Leeds United team skippered by Gary Kelly and including his nephew Ian Harte won 1-0 at Elland Road and drew 1-1 at the San Siro.
As Milan only finished eighth in Serie A last year their European trips this season are restricted to preseason friendlies. Despite this, their visit to Ireland on Saturday probably isn’t even their most important fixture of the weekend, as on Sunday they face Chelsea at Stamford Bridge, in a fixture only announced after tens of thousands of tickets for the Leeds game had already been sold.
The demands of playing two matches in different capital cities on consecutive days means that star names such as Rafael Leao, Christian Pulisic and new signing Luka Modric may not feature in Dublin. This makes sense from a workload perspective but whether those Irish fans paying €126 for their ticket agree remains uncertain.
Preseason friendly: Leeds United v AC Milan, Saturday, Aviva Stadium, 3pm
