Ange Postecoglou has learned his Tottenham side will face opposition from either the Netherlands, Turkey, Denmark or Spain in their Europa League last-16 clash.
Postecoglou, who was given some respite from his struggles on Thursday when Spurs qualified automatically for the knockout stage of Europe's second-string Cup competition, had the club's path towards a potential final in Bilbao narrowed down for them in Friday's play-off round draw.
In the last 16, Spurs will face either the winners of the play-off between Dutch side AZ Alkmaar and Turkey’s Galatasaray, or the victors in the tie between Denmark’s FC Midtjylland vs Spain’s Real Sociedad.
Fellow Premier League outfit Manchester United, kept apart from Spurs on the other side of the draw, will also meet one of those same four sides in the last 16.
Meanwhile, Postecoglou, under the cosh with his side lying 15th in the Premier League, was given a vote of confidence from the man who could make life even more difficult for him this weekend, Brentford boss Thomas Frank.
Before their match at Brentford's Gtech Community Stadium on Sunday, Frank said he believed Postecoglou could turn Tottenham's fortunes around and even win a trophy.
"We were also hit very hard by injuries last year so, from that perspective, I understand the situation Ange is in now at Tottenham," Frank said.
"When results are also not going your way, that's tough. They're things we need to deal with as managers and I'm convinced that Ange is doing that well and he will get through it.
"He doesn't need advice, but he just needs to trust his own processes and trust what he believes in, which he does and that's the main thing.
"I have massive respect for Ange. Speaking for myself, it is tough at times and feels like you're carrying everything on your shoulders.
"He's done very well to keep going and keep believing. Maybe, in one of his toughest moments, they will win a trophy, which will be massive for Tottenham.
"It could be one of those seasons where they suffer incredibly - and maybe they suffer even more - but they win a trophy."
Spurs handed Brentford a 3-1 defeat in the reverse fixture in September and, as speculation about his future increases, it's a match that Postecoglou desperately needs to win.
EUROPA LEAGUE PLAY-OFFS DRAW
Twente (Netherlands) v Bodo/Glimt (Norway)
Fenerbahce (Turkey) v Anderlecht (Belgium)
Union Saint-Gilloise (Belgium) v Ajax (Netherlands)
POAK (Greece) v FCSB (Romania)
AZ Alkmaar (Netherlands) v Galatasaray (Turkey)
Midtjylland (Denmark) v Real Sociedad (Spain)
Ferencvaros (Hungary) v Viktoria Plzen (Czechia)
Porto (Portugal) v Roma (Italy)
With PA
