Robin van Persie faces a difficult task if he is to set up a potential tie with Manchester United in the Champions League play-offs after Fenerbahce were drawn against Shakhtar Donetsk in the third qualifying round.
The Turkish club returns to UEFA competitions after a two-year ban for match-fixing, with former United players Van Persie and Nani needing to overcome a two-legged affair with the Ukrainian Premier League runners-up to progress.
Were Fenerbache to prevail, Vitor Pereira’s side would be unseeded in the League Route of the play-off round, while United would enter the competition as a seeded club based on their current UEFA coefficient ranking.
Elsewhere, Celtic face a trip to Azerbaijan or Montenegro in the next round after being drawn to play Qarabag or Rudar Pljevlja.
Ronny Deila’s men must beat Stjarnan in the second round, and the Scottish champions take 2-0 advantage to Iceland for the second leg next Wednesday.
Qarabag drew 0-0 at home to Rudar in Azerbaijan in the first leg.
Meanwhile, last season’s quarter-finalists Monaco have been paired with Young Boys, Ajax drew Rapid Vienna, CSKA Moscow host the first leg with Sparta Prague and Panathinaikos face Bruges.
The Greek side could go straight into the group stage, however, with domestic champions Olympiakos implicated in an ongoing criminal match-fixing investigation that could result in them being expelled from the competition.
In a separate draw for national champions, Basel, who reached the last 16 last season, will play either Lech Poznan or Sarajevo.
The first-leg matches will be played on July 28-29, with the return fixtures on August 4-5.
CHAMPIONS LEAGUE THIRD QUALIFYING ROUND DRAW
Panathinaikos (Greece) vs. Bruges (Belgium)
Young Boys (Switzerland) vs. Monaco (France)
CSKA Moscow (Russia) vs. Sparta Prague (Czech Republic)
Rapid Vienna (Austria) vs. Ajax (Netherlands)
Fenerbahce (Turkey) vs. Shakhtar Donetsk (Ukraine)
Sarajevo (Bosnia-Herzegovina) or Lech Poznan (Poland) vs. Basel (Switzerland)
Ludogorets Razgrad (Bulgaria) or Milsami Orhei (Moldova) vs. Skenderbeu (Albania) or Crusaders (Northern Ireland)
HJK Helsinki (Finland) or Ventspils (Latvia) vs. Maribor (Slovenia) or Astana (Kazakhstan)
Celtic (Scotland) or Stjarnan (Iceland) vs. Qarabag (Azerbaijan) or Rudar Pljevlja (Montenegro)
Trencin (Slovakia) or Steaua Bucharest (Romania) vs. Partizan (Serbia) or Dila Gori (Georgia)
Midtjylland (Denmark) or Lincoln Red Imps (Gibraltar) vs. APOEL (Cyprus) or Vardar (Macedonia)
Hibernians (Malta) or Maccabi Tel-Aviv (Israel) vs. Viktoria Plzen (Czech Republic)
Fola Esch (Luxembourg) or Dinamo Zagreb (Croatia) vs. Molde (Norway) or Pyunik (Armenia)
The New Saints (Wales) or Videoton (Hungary) vs. BATE Borisov (Belarus) or Dundalk (Ireland)
Salzburg (Austria) vs. Malmo (Sweden) or Zalgiris Vilnius (Lithuania)