Arsenal must bypass Turkish giants Fenerbahce in order to qualify for this season's Champions League group stage after the play-off draw in Nyon.
The Gunners faced Fenerbahce during the 2008/09 Champions League group stage, drawing 0-0 at home before a 5-2 away win in Turkey.
Fenerbahce are eligible to play in the play-off phase after the Court of Arbitration for Sport temporarily lifted their two-year ban from competing in European competition, following a Uefa investigation into match fixing.
The club will discover their fate after completing the play-off round meaning they could be replaced by Kayserispor in the group phase, who finishined fifth in Super Lig last season, should they beat Arsenal but subsequently have their appeal upheld by CAS.
Scottish League champions Celtic meanwhile face a daunting trip to Kazakhstan to face Shakhter Karagandy in their play-off tie.
Neil Lennon's side narrowly beat Elfsborg 1-0 on aggregate to in the third knock-out round and will face the Kazak league champions of 2012 in order to qualify for the group stage.
Elsewhere in the draw, PSV Eindhoven and AC Milan will face-off in a repeat of the 2004/05 semi-final while Lyon will take on Real Sociedad.
The ties will be played on the 20 and 21 August and 27 and 28 August.
Champions League Play off draw in full:
Dinamo Zagreb v FK Austria Vienna
Ludogorets v Basle
Plzen v Maribor
Shakhter Karagandy v Celtic
Steaua Bucuresti v Legia Warsaw
Lyon v Real Sociedad
Schalke 04 v FC Metalist Kharkiv
Pacos Ferreira v Zenit St Petersburg,
PSV v AC Milan,
Fenerbahce v Arsenal