18 October 1908, the first Madonnina derby is not played in Milan. But in Switzerland

On 18 October 1908, the Coppa which takes the name of the city was staged in Chiasso. An invitational tournament which however sees the participation of two teams from Milan. On the one hand, Milan, who have already won twice and as for the Rimet Cup (to come, two decades later) if they were to make it three of a kind they would keep the cup, while on the other side there is Inter , in the debut edition, given that the foundation of the Nerazzurri club dates back only seven months. It is the first Milanese derby in history, with many Ticino fans who watched the match due to the proximity that Chiasso has to Milan.

Two halves of 25 minutes each, with Milan winning 2-1. The goals were scored by Lana and Forlano for the Rossoneri, then Payer in return for the Nerazzurri. In reality it was the final of the event, given that Milan had defeated Circolo Juventus Bellinzona 2-0 in the quarter-final, while Inter had beaten Ausonia 1-0. Only one semi-final had been played because there was no time, so Milan eliminated Chiasso 2-0, Inter won on the nickel, reaching the last act thanks to the grace received. It won’t be enough to win the first derby ever played outside the national borders. In front of two thousand spectators, Milan took home the Chiasso Cup definitively.

Here are the lineups from that match.
Milan
Radice, Glaser, Sala, Bianchi, Steltzer, Meschia, Lana, Mädler, Forlano, Leich, Colombo.

Inter
Campelli, Fronte, Zoller, Yenni, Fossati, Stebler, Capra, Peyer, Peterly, Aebi, Schuler.