Arsenal have been paired with Besiktas during Friday's Champions League play-off draw in Nyon, Switzerland.
Arsene Wenger's men last made it past the round of 16 in 2009-10 and will be determined to do better this term, yet they will have to see off the Turks first, who last featured in European club football's elite competion 2009-10.
In what is arguably the standout tie of the play-offs, Rafael Benitez's Napoli will have to deal with La Liga representatives Athletic Bilbao if they are to reach the group stages.
The Serie A outfit impressed in the Champions League three years ago, yet were eliminated in the group stages last term. Athetic, meanwhile, have appeared in the Champions League just once before, when they crashed out in the group stages in 1998-1999.
Furthermore, Lille meet Porto, while Bayer Leverkusen take on Copenhagen and Standard Liege will have to battle Zenit in the final tie of the league route.
In the champions route, Celtic - who were allowed back in the tournament at the expense of Legia Warsaw following an administrative error by the Poles - were paired with Maribor.
The opening legs will be played on August 19 and 20, with the return games on August 26 and 27, the 10 winners joining the 22 teams automatically qualified for the group stage.
Maribor (SVN) VS Celtic (SCO)
Salzburg (AUT) VS Malmo (SWE)
Aalborg (DEN) VS APOEL (CYP)
Steaua Bucharest (ROU) VS Ludogorets (BUL)
Slovan Bratislava (SVK) VS BATE (BLR)
Besiktas (TUR) VS Arsenal (ENG)
Standard Liege (BEL) VS Zenit St Petersburg (RUS)
Copenhagen (DEN) VS Bayer Leverkusen (GER)
Lille (FRA) VS Porto (POR)
Napoli (ITA) VS Athletic Bilbao (ESP)