Former European champions AC Milan and PSV Eindhoven will meet in the play-offs while 1967 winners Celtic FC face Kazakh newcomers FC Shakhter Karagandy.
Seven-time European champions AC Milan will take on 1988 winners PSV Eindhoven for a place in the UEFA Champions League group stage following the play-off draw in Nyon.
The tie of the round will evoke memories of the sides' 2004/05 semi-final which the Rossoneri, the most decorated club in the draw, won on away goals after a 3-1 second-leg loss featuring a double from Phillip Cocu (now PSV coach). The following season the teams met in the group stage, with PSV drawing 0-0 at San Siro and winning 1-0 at home.
Elsewhere in the league route, Portuguese debutants FC Paços de Ferreira tackle FC Zenit St Petersburg, Arsenal FC play Fenerbahçe SK and Real Sociedad de Fútbol make their return to the competition after a decade away against Olympique Lyonnais. The Ligue 1 outfit eliminated La Real 2-0 on aggregate in the 2003/04 first knockout round.
In the champions route, 1967 victors Celtic FC face a trip into the unknown against FC Shakhter Karagandy – the first Kazakh representatives to reach this stage. FC Basel 1893, UEFA Europa League semi-finalists last term, were paired with PFC Ludogorets Razgrad.
The first legs take place on 20/21 August, with the returns a week later. The ten winners will join the 22 automatic entrants in the UEFA Champions League group stage, the draw for which is held in Monaco on Thursday 29 August. The losers will proceed to the UEFA Europa League group stage. The final will be played at the Estádio do Sport Lisboa e Benfica on Saturday 24 May.
UEFA Champions League play-off draw
Olympique Lyonnais (FRA) v Real Sociedad de Fútbol (ESP)
FC Schalke 04 (GER) v FC Metalist Kharkiv (UKR)
FC Paços de Ferreira (POR) v FC Zenit St Petersburg (RUS)
PSV Eindhoven (NED) v AC Milan (ITA)
Fenerbahçe SK (TUR) v Arsenal FC (ENG)
GNK Dinamo Zagreb (CRO) v FK Austria Wien (AUT)
PFC Ludogorets Razgrad (BUL) v FC Basel 1893 (SUI)
FC Viktoria Plzeň (CZE) v NK Maribor (SVN)
FC Shakhter Karagandy (KAZ) v Celtic FC (SCO)
FC Steaua Bucureşti (ROU) v Legia Warszawa (POL)
The participation of Fenerbahçe SK and FC Metalist Kharkiv in the competition is subject to pending disciplinary and CAS proceedings.