Tottenham have been handed a daunting group in the Europa League including a long haul trip to Azerbaijan.
Spurs were drawn in Group J with Monaco, Anderlecht and FK Qarabag, who play matches in Azerbaijan's capital Baku.
However there was better news for the North London outfit with the club confirming the signing of Son Heung-Min from Bayer Leverkusen.
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Liverpool's task is also not straightforward with games against Russian side Rubin Kazan, Bordeaux and Swiss club Sion in Group B.
Yet Brendan Rodgers may be able to call upon Daniel Sturridge - who has now returned to full training having not featured since April.
Celtic have the prospect of facing Robin van Persie and Nani's new side Fenerbahce plus Ajax and Molde from Norway in Group A.
It will be the pair's first return to the United Kingdom since moving from Manchester United in the summer.