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Arsenal have been drawn against FC Twente, managed by former England boss Steve McClaren, in the Champions League third qualifying round.
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Twente were fourth in the Dutch Eredivisie last season and are McClaren’s first team since he was sacked by England last autumn after failing to qualify for Euro 2008.
McClaren said: “I think of all the teams we could have had, that is the toughest – or one of the toughest.
“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.”
2005 winners Liverpool face a relatively straightforward task against Belgian champions Standard Liege.
Last season’s UEFA Cup finalists Rangers will face either Aalborg, champions of Denmark, or Bosnian side Modrica.
However, Walter Smith’s side must first see off FBK Kaunas in their second qualifying round match, having drawn the first leg 0-0 at Ibrox on Wednesday.
Away from the British sides, the plum tie is Schalke against Atletico Madrid. The Bundesliga side reached the final 16 last season, while Atletico are hoping to end a long exile from the Champions League proper after a fourth-place finish in La Liga last season.
Juventus face either Tampere of Finland or Slovakia’s Artmedia Bratislava, while Barcelona take on either Beitar Jerusalem or Wisla Krakow.
Matches will be played on August 12/13 and 26/27, with the winners going through to the group stage.
Champions League third qualifying round
Anorthosis/Rapid Vienna v Olympiacos
Vitoria Guimaraes v Gothenburg/Basel
Shakhtar Donetsk v Domzale/Dinamo Zagreb
Schalke v Atletico Madrid
Aalborg/Modrica v Rangers/Kaunas
Barcelona v Beitar Jerusalem/Wisla Krakow
Levski Sofia v Anderlecht/BATE Borisov
Standard Liege v Liverpool
Inter Baku/Partizan v Fenerbahce/MTK Budapest
FC Twente v Arsenal
Spartak Moscow v Drogheda/Dynamo Kiev
Juventus v Tampere/Artmedia
Brann/Ventspils v Marseille
Fiorentina v Slavia Prague
Galatasaray v Steaua Bucharest
Panathinaikos/Dinamo Tbilisi v Sheriff/Sparta Prague
