Arsenal have been pitched into a Champions League legal minefield after being paired with Turkish giants Fenerbahce for a place in the group phase.
Arsene Wenger’s side have to travel to Istanbul and the intimidating Sucru Saracoglu Stadium on August 21, with the return leg six days later.
It was the toughest of the five possible opponents could have drawn, with AC Milan forced to take on PSV Eindhoven in the other crunch clash.
With Luis Suarez having said the prospect of playing Champions League football explains why he wants to leave Liverpool for Arsenal, the result of the games could impact on the Uruguayan’s status.
But Wenger’s men may find themselves with a free pass to the elite stage even if they slip up over two legs as Fenerbahce are currently banned by UEFA.
The Istanbul outfit’s former president, Aziz Yildirim, was jailed last September following an investigation into match-fixing allegations after their title win in 2011.
UEFA ruled earlier this summer that officials at the club were complicit in the match-fixing and imposed a European ban which was placed on hold after Fenerbahce appealed to the Swiss-based Court of Arbitration for Sport.
But CAS won’t announce their verdict on August 28 – the day after the tie’s potentially decisive second leg.
If the UEFA verdict is upheld, the Gunners would be reinstated even if they have been knocked out on the field.
Arsenal would then either be placed into the group stage – the draw takes place in Monaco on August 29 – or face ANOTHER play-off against Austrian side Salzburg, who were beaten on aggregate by Fenerbahce in the second knock-out round this week.
Fenerbahce were Europa League semi-finalists last season and, in a twist of fate, include former Anfield favourite Dirk Kuyt as well as ex-Everton defender Joseph Yobo and one-time Newcastle midfielder Emre.
Emre, now the Fenerbahce skipper, was key to Inter Milan’s 3-0 win over Arsenal at Highbury in 2003.
He said: "Arsenal are one of the exponents of total football, one of the most famous teams in the world. But they are a young team and if we play well we have a chance against them.
"We want to gain an advantage by getting a good result in the first match with the support of our fans."
Play-off round draw in full
(Ties to be played August 20/21 and 27/28)
Dinamo Zagreb v Austria Vienna
Ludogorets v Basle
Plzen v Maribor
Shakhtyor Karaganda v Celtic
Steaua Bucharest v Legia Warsaw
Lyon v Real Sociedad
Schalke v Metalist Kharkiv
Pacos Ferreira v Zenit St Petersburg
PSV Eindhoven v AC Milan
Fenerbahce v Arsenal