1963: a tough start against Inter
Competing in the European Cup for the second time following their domestic double the previous season, AS Monaco took on Inter Milan in the last 16. Lucien Leduc's side held on for over an hour in the first leg at the San Siro, but lost the game 1-0. There was all to play for in the return leg, but a brace from Mazzola on 14 and 19 minutes poured cold water on Monegasque hopes. The final score was 1-3. It would be AS Monaco's last appearance in the European Cup for some time, while Internazionale were destined to become European champions for the first time.
1990: just one step away from the final...
After knocking out Belenenses, Dynamo Berlin and Valladolid, Arsène Wenger's men lost in the Cup Winners Cup semi-final to a Sampdoria team inspired by the sparkling Gianluca Vialli. Weah opened the scoring in the first leg, but the Italian striker netted twice. Diaz equalised with ten minutes to go, but the return leg in Genoa looked a daunting prospect. And so it turned out, as Vierchowod scored for Sampdoria in the 9th minute, before Lombardo put the tie to bed on 57 minutes. "Samp" would go on to beat Anderlecht in the final.
*Having lost in the final of the Coupe de France the previous season, AS Monaco qualified for the 1989-1990 Cup Winners Cup thanks to OM's league and cup double.
1992: Roma beaten!
After their unhappy experience against Sampdoria two years earlier, the Red & Whites produced an upset in the quarter-final of the Cup Winners Cup against Roma, who boasted some big name players like Aldaïr, Thomas Hässler and Rudy Völler. The first leg was played at the Stadio Olimpico, and AS Monaco kept their chances alive with a goalless draw. The return leg was a magical night as Rui Barros (1m60) scored with a header just before the break to send AS Monaco through. The Red & Whites went on to reach the final, where they lost to Werder Bremen.
1994: Milan far too strong
For their first appearance in the new-look "UEFA Champions League", the Red & Whites reached the semi-final after finishing second in their group behind Barcelona. Back then, there were no home and away fixtures at that stage of the competition. Milan, who topped the other group, had home advantage and duly made the most of it. Desailly opened the scoring in the 14th minute, but a red card for Costacurta in the 40th minute gave AS Monaco hope. That hope was quickly snuffed out though, as Albertini put the Italians further ahead on 48 minutes and Massaro settled matters definitively in the 65th minute (final score: 3-0). In the final, Milan hammered Barcelona 4-0!
1997: Inter get a fright
AS Monaco enjoyed an excellent run in the UEFA Cup that year, disposing of Krakow, Moenchengladbach, Hamburg and Newcastle along the way. In the semi-finals, they faced Youri Djorkaeff's Inter Milan, who were the favourites. The first half of the first leg at the San Siro set the tone for the tie, as Inter scored three goals to rattle Jean Tigana's side. Ikpeba pulled one back to leave AS Monaco with hopes of a comeback in the second leg, which looked on the cards when the Nigerian scored on 69 minutes at the Louis-II. AS Monaco won on the night, but were unable to come up the goal needed to qualify. in the final, Inter were beaten by Schalke 04.
1998: another semi-final defeat!
After knocking out Manchester United in the quarter-final, AS Monaco took on a Juventus side that included the likes of Zidane, Deschamps, Del Piero and Edgar Davids... Once again, the Red & Whites went down at the final hurdle as "Juve" won the first leg 4-1 in utterly dominant fashion. AS Monaco knew that the final was beyond them, but made it a point of honour to win the second leg, which they did 3-2, going out of the competition with their heads held high. Juventus were beaten by Real Madrid in the final. Altogether, AS Monaco have reached the semi-final stage of a European competition on seven occasions, making it to the final twice, but losing five other semis against clubs from Italy... They have won just once before against Italian opposition, and that was in a quarter-final... An omen, maybe?