Former England manager Steve McClaren will face Arsenal with his new club Twente Enschede after the teams were paired in the Champions League third qualifying round draw on Friday.
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McClaren took the reins of the Dutch club during the close season for his first coaching role since leaving the England job last November, following the failure to qualify for Euro 2008.
However, he faces a tough task in trying to outwit Arsenal, Champions League finalists in 2006 and quarter-finalists last season, when the sides meet for a place in the group stage.
McClaren, who led Middlesbrough to the 2006 UEFA Cup final, told SkySports: "I expected one of the English teams - fate deals you certain cards and it has dealt us this card. On one hand it is very, very tough -- we know that -- but on the other very exciting."
Spanish side Atletico Madrid will not have it easy against another of last term's quarter-finalists, Germany's Schalke 04, in what should be one of the most intriguing contests of the third qualifying round, to be played later this month.
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Atletico are seeking a return to the Champions League for the first time since the 1996/97 season.
Of the other big names in the draw, five times winners Liverpool face Belgian champions Standard Liege while Barcelona take on the winners of the Beitar Jerusalem v Wisla Krakow second qualifying round tie.
Italian giants Juventus must beat either Artmedia Bratislava or Finnish side Tampere United if they are get back into the group stage after an absence of two seasons.
Turkish champions Galatasaray were drawn against former European Cup winners Steaua Bucharest while Olympique Marseille, who lifted the trophy in 1993, will play either Norway's Brann Bergen or Ventspils of Latvia.
Scottish side Rangers are likely to face Danish champions Aalborg, coached by former Scotland midfielder Bruce Rioch, if they can get past Kaunas in the second leg of their second qualifying round tie next week, having drawn 0-0 on Wednesday.
The first legs will be played on August 12-13 with the ties concluding on August 26-27. The group stage begins on September 16.
Third qualifying round draw
First leg: 12/13 August
Second leg: 26/27 August
Anorthosis Famagusta FC (CYP) / SK Rapid Wien (AUT) v Olympiacos CFP (GRE)
Vitória SC (POR) v IFK Göteborg (SWE) / FC Basel 1893 (SUI)
FC Shakhtar Donetsk (UKR) v NK Domale (SVN) / NK Dinamo Zagreb (CRO)
FC Schalke 04 (GER) v Club Atlético de Madrid (ESP)
Aalborg BK (DEN) / FK Modriča (BIH) v Rangers FC (SCO) / FBK Kaunas (LTU)
FC Barcelona (ESP) v Beitar Jerusalem FC (ISR) / Wisla Kraków (POL)
PFC Levski Sofia (BUL) v RSC Anderlecht (BEL) / FC BATE Borisov (BLR)
R. Standard de Liège (BEL) v Liverpool FC (ENG)
FC İnter Bakı (AZE) / FK Partizan (SRB) v Fenerbahçe SK (TUR) / MTK Budapest (HUN)
FC Twente (NED) v Arsenal FC (ENG)
FC Spartak Moskva (RUS) v Drogheda United FC (IRL) / FC Dynamo Kyiv (UKR)
Juventus (ITA) v Tampere United (FIN) / FC Artmedia Petralka (SVK)
SK Brann (NOR) / FK Ventspils (LVA) v Olympique de Marseille (FRA)
ACF Fiorentina (ITA) v SK Slavia Praha (CZE)
Galatasaray AS (TUR) v FC Steaua Bucureşti (ROU)
Panathinaikos FC (GRE) / FC Dinamo Tbilisi (GEO) v FC Sheriff (MDA) / AC Sparta Praha (CZE)