Benfica begin their Europa League campaign against AC Milan on Wednesday at the San Siro in Milan for what is considered their toughest fixture in the league phase.
The Portuguese side, managed by head coach Marco Silva, face a formidable test against Ruben Amorim's team in UEFA's secondary European club competition.
AC Milan hold an undefeated historical record against Benfica in official matches, having recorded four victories and two draws in their previous six meetings.
That dominant record includes two famous victories in European Champion Clubs' Cup finals, with Milan defeating the Lisbon club 2-1 in 1963 and securing a 1-0 win in 1990.
Head to head record and team news
The Italian hosts feature two former Benfica players in their squad, with forward Gonçalo Ramos and winger Diego Moreira now playing for the Rossoneri.
Moreira, who has become a Belgian international, proved decisive for Milan on Saturday by scoring both goals in a 2-2 draw away against Lazio.
That result marked a second draw in four matches for Milan, who remain unbeaten this season and sit sixth in Italy's Serie A.
Benfica form and European campaign
Benfica return to the Europa League this season after five consecutive campaigns competing in the elite UEFA Champions League.
The Portuguese club reached the final of the Europa League in both the 2012/13 and 2013/14 seasons, having also finished as runners up in the predecessor UEFA Cup back in 1982/83.
Marco Silva's side navigated three qualifying rounds to earn their spot in this season's league phase.
They enter Wednesday's clash in outstanding form, riding a run of seven consecutive victories across the Portuguese I Liga and European qualifiers.
Benfica have displayed remarkable attacking power during this run, scoring 40 goals across 12 matches in all competitions so far this season.
Match details and other fixtures
The match at the Estádio Giuseppe Meazza in San Siro kicks off at 21:00 local time, which is 20:00 in Lisbon.
Australian referee Jarred Gillett, who regularly officiates matches in England's Premier League, will take charge of the fixture.
Wednesday's European schedule also features a meeting between two Portuguese managers, as Vítor Bruno leads Belgian side Anderlecht at home against Paulo Fonseca's Lyon.
On Thursday, Portuguese Cup winners Torreense make their historic European debut when the surprising Taça de Portugal champions face Norwegian club Lillestrom.
