Milan took on Athlone Town in the 1974/75 UEFA Cup, drawing 0-0 in their away first leg before going on to claim a more comfortable result in the second leg.
Rovers’ form might give Milan slight cause for concern though, with the Hoops topping the League of Ireland, boasting an eight-point lead as they are still unbeaten in their 11 games so far.
The Irish side do have previous against Italian opposition as they faced Juventus in the Europa League’s third qualification round in 2010/11.
Shamrock Rovers: Mannus; O’Brien, Lopes, Grace; Finn, McEneff, O’Neill, J Byrne, Farrugia; Burke, Greene
AC Milan: G. Donnarumma; Calabria, Kjaer, Gabbia; Theo Hernandez; Kessie, Bennacer; Castillejo, Calhanoglu, Saelemaekers; Ibrahimovic