Glasgow Rangers, who recently returned from a demoralising Champions League elimination in Turkey, have been handed a daunting trek to war-torn southern Russia as scant consolation in the first round of the UEFA Cup.
Dick Advocaat's side were paired with the Russian team Anzhi Makhachkala, situated on the shores of the Caspian Sea, in yesterday's draw in Monaco. While the Dagestani town is known for its oil, caviar and brandy, it is only 100 miles from troubled Grozny and the Scots will take counsel from the British Foreign Office before making the seven-hour flight.
"It's about as far away as we could be in terms of European football," admitted Rangers' secretary Campbell Ogilvie. "Geographically, it's a difficult place. We went to Vladikavkaz in 1996 so we know a bit about what to expect; we didn't have any trouble then, but we will talk to the Foreign Office before we go. They may find matters somewhat easier on the pitch at the 10,000-capacity Trud stadium.
Formed in 1992, this is Anzhi's first venture into European competition but having finished fourth in the Russian league last season, they only qualified as losing cup finalists - they were beaten 4-3 on penalties by Lokomotiv Moscow. Not that Rangers, perennial European underachievers, will be taking anything for granted.
"We don't know much about their strength, but if they are competing in the UEFA Cup they must be quite strong," added Ogilvie. "Obviously, we are still disappointed at not being in the Champions League, but we have to face the facts. Let's try and be positive.
Ipswich Town return to continental competition after an 18-year absence and 20 years after they won the UEFA Cup, against another Russian side, Torpedo Moscow.
While the Suffolk team have never competed in Moscow before, they were the first English club to sign a Soviet player when they bought Sergei Baltacha from Dynamo Kiev in 1988.
"I was sent over to Moscow by our chairman, Patrick Cobbold, to negotiate the transfer," recalled the Ipswich chairman David Sheepshanks. "We'd sent a telex and as far as we were concerned it was a matter of simply finalising the details. But they frogmarched Sergei in to the Russian Football Association and claimed they knew nothing of the deal. "As it was, we had a six-hour lunch consuming vast amounts of vodka while desperately attempting to remain sober, before we clinched his signing. It was a revealing introduction to life in Russia."
Baltacha - whose son Sergei plays for St Mirren and daughter Helena reached the semi-finals of Junior Wimbledon this year - is now coaching in Scotland.
"We will talk to Sergei about the game, but it is thrilling to be back playing on this stage," added Sheepshanks. "It is possibly the toughest draw we could have got in our group, but we are all very excited."
After a season of barnstorming performances in the Champions League, Leeds bump back down to Earth in the UEFA Cup with a trip to the Portuguese club CS Maritimo.
The Yorkshire side will be familiar with their surroundings on Madeira having edged past these opponents in this competition two years ago - a tie which proved to be George Graham's last before he left to manage Tottenham Hotspur. "We scraped through after a penalty shoot-out," said the Leeds chairman Peter Ridsdale, "so it is etched in my memory. But we were treated wonderfully well in Madeira and stayed with the president in his palace, which was stunning."
The surroundings may be somewhat less grandiose for Chelsea, who successfully avoided St Gallen - the Swiss club knocked them out of this competition 2-1 on aggregate last season - but instead face a testing tie against Levski Sofia.
Levski finished seven points clear at the top of the Bulgarian league last year and have won their opening two fixtures this term.
"We'll have to have them watched," said the Blues' managing director Colin Hutchinson. "This is a tough competition, although it is devalued a little by the hype surrounding the Champions League. I'm sure we've got players in our side who will know about their strengths and weaknesses."
Aston Villa's reward for slogging through the Intertoto Cup is a trip to Croatia to play NK Varteks, whose chairman Andjelko Herjavac was killed recently in a car crash. John Gregory's side defeated the Croats Slaven Belupo in the summer competition and will take advice from their new striker Bosko Balaban, who was granted a work permit yesterday, about their opponents.
"They aren't a bad side at all," warned the former West Ham and Everton defender Slaven Bilic. "They won 5-1 in Hajduk Split and, in Veldin Karic, they have a dangerous striker who has already played in Italy with Torino."
The two other Scottish sides involved, Kilmarnock and Hibernian, face tricky ties with Viking Stavanger - a breeding ground for young Norwegian talent - and AEK Athens.
The Draw
First Round: Inter Bratislava v Liteks Lovetch; Inter Milan v Brasov; Servette v Slavia Prague; Roda JC v Fylkir; CSKA Kiev v Crvena Zvezda; Genclerbirligi v Halmstad; AEK Athens v Hibernian; Olimpija Ljubljana v Brondby; FC Utrecht v Graz AK; Slovan Bratislava v Liberec; FC Copenhagen v FK Obilic; CSKA Sofia v Shakhtar Donetsk; Standard Liege v Strasborg; AC Milan v BATE Borisov; Chernomorets v Valencia; Aston Villa v Varteks; Parma v HJK Helsinki; HIT Garico v Osijek; Ipswich v Torpedo Moscow; Kilmarnock v Viking FK; Ajax v Apollon Limassol; Real Zaragoza v Silkeborg IF; Dinamo Bucharest v Grasshoppers; Dukla Pribram v Sedan; Troyes v MSK Ruzomberok; Legia Warsaw v Elfsborg; Westerlo v Hertha Berlin; Chelsea v Levski Sofia; PAOK Salonika v FC Karnten; Dinamo Moscow v Birkirkara; Dnipro v Fiorentina; St Gallen v Steaua Bucuresti; Bordeaux v Debrecen; Gaziantepspor v Hapoel Tel-Aviv; FC Haka v Union Berlin; Partizan Belgrade v Rapid Vienna; Celta Vigo v Olomouc; Sporting Lisbon v FC Midtjylland; Anzhi Makhachkala v Rangers; Hajduk Split v Wisla Krakow; PSG v Rapid Vienna; Maritimo v Leeds; Olympiakos Nicosia v Club Brugge; Odds BK v Helsingborg; Tirol Innsbruck v Zizkov; Dynamo Zagreb v Maccabi Tel-Aviv; Polonia Warsaw v FC Twente; SKM Puchov v Freiburg.
Ties will be played on September 13th and 27th