Arsenal must overcome Serie A opposition in the shape of Udinese if Arsene Wenger's team are to make it to the UEFA Champions League group stages for the 14th successive season.
The Gunners were pitted against the Italian side in the draw for the Champions League play-offs held at UEFA headquarters in Nyon today.
This will be a first-ever meeting between Arsenal, the beaten finalists in 2006, and Udinese, who last made it into the group stage that same season.
The draw also featured two previous winners of Europe's top club competition, with Bayern Munich facing Swiss side FC Zurich and former title-holders from Portugal, Benfica, up against Dutch league runners-up FC Twente.
Bayern have been crowned champions of Europe four times and their coach Jupp Heynckes said: "This is a game we can win and an interesting task. We have a great opportunity to move into the group stage."
But Heynckes insisted he would not be taking the Swiss team lightly. "Swiss football is very strong," he said. "Last season, Zurich finished just one point behind Basel, that says a lot for the quality of the club. We will be watching them this weekend. Sometimes the supposedly weaker is actually the stronger one."
Malmo, who knocked out Scottish giants Rangers in the third qualifying round this week, were rewarded with a match-up against Croatian league champions Dinamo Zagreb.
Russian outfit Rubin Kazan, who caused a stir when beating Barcelona 2-1 in the group stage two seasons ago, will not prove easy pickings for Lyon of France. Rubin booked their play-off place with a 4-1 aggregate qualifying win over Dynamo Kiev.
The first legs will be played on 16/17 August with the second legs the following week. The ten play-off winners will then join the 22 automatically qualified teams for the group stage draw to be held in Monaco on 25 August.
The final for this season's competition will be held at Bayern's stadium in May next year.
UEFA Champions League play-offs draw:
Wisla Krakow (POL) v Apoel Nicosia (CYP)
Maccabi Haifa (ISR) v Genk (BEL)
Dinamo Zagreb (CRO) v Malmo (SWE)
FC Copenhagen (DEN) v FC Viktoria Plzen (CZE)
FC BATE Borisov (BLR) v Sturm Graz (AUT)
OB Odense (DEN) v Villarreal (ESP)
FC Twente (NED) v Benfica (POR)
Arsenal (ENG) v Udinese (ITA)
Bayern Munich (GER) v FC Zurich (SUI)
Lyon (FRA) v Rubin Kazan (RUS)