Tottenham Hotspur
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Borussia Monchengladbach
VfB Stuttgart
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Sparta Rotterdam
PSV Eindhoven
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2:00 AM UTC Oct 26, 2016
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Cerro Porteño
Independiente Medellín
12:00 AM UTC Oct 26, 2016
Leg 2Aggregate: 0 - 0
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New club, same remit for AVB

It was a season of frustration and heartache for Spurs last season. After finishing fourth in the Premier League, they were denied a place in the Champions League when sixth-placed Chelsea defied the odds to win Europe's flagship competition and supplant them in this season's tournament.

It was a blow to morale at White Hart Lane, and dented Tottenham's chances of retaining the services of want-away midfielder Luka Modric. But, in truth, Spurs should have had third place sewn up and pointed the finger of blame in one direction for throwing it away.

In February, with the White Hart Lane side ten points clear of North London rivals Arsenal, the wheels came off in dramatic fashion when manager Harry Redknapp was installed as favourite to succeed Fabio Capello as England boss after the Italian walked out on the national team.

Redknapp, who didn't get the England job in the end, insisted the speculation was no distraction to him and his players but, as Spurs haemorrhaged points and limped into fourth place, chairman Daniel Levy disagreed and sacked his manager.

The man charged with taking Tottenham back into the Champions League is Andre Villas-Boas, who was fired by Chelsea after 27 league matches at Stamford Bridge. It's a big gamble by Levy, and Villas-Boas must quickly get to grips with a number of key issues at White Hart Lane if he is to emulate his success at FC Porto - where he won the treble - rather than reprise his lack of it with the Blues.

Firstly, he must convince the players that he is the right man for the job. His attempt to revolutionise Chelsea in terms of personnel and style didn't go down too well with their influential players, but Spurs seem more predisposed to the AVB masterplan and have the players to carry it out.

In Gareth Bale and Aaron Lennon, they have two of the quickest wingers in the league, and with attack-minded full-backs Kyle Walker and Benoit Assou-Ekotto offering support down the flanks, the Portuguese already has the framework upon which to build the fast-paced approach that proved such a success at Porto.

In the centre of defence, Spurs stalwart Ledley King may have called time on a career plagued by dodgy knees, but new signing Jan Vertonghen is a ball-playing defender who should dovetail brilliantly with either Michael Dawson or Younes Kaboul, with William Gallas in reserve.

Villas-Boas' real problems begin in midfield, where a creative gap will be left if Modric leaves the club after a summer of transfer speculation. One option would be to drop Rafael van der Vaart into midfield but the Dutchman, who operates primarily as a support striker, barely lasted a full 90 minutes last season and offers little defensively.

New signing Gylfi Sigurdsson, who impressed at Swansea while on loan from German side Hoffenheim last term, is probably the best fit. The Icelander, who was also a summer target for Liverpool, is a quality footballer - but starring in a newly-promoted side and replacing one of the best creative midfielders in Europe are two different things. There is also talk of Joao Moutinho arriving from Porto to help plug the gap.

One department in which new faces will need to arrive is in attack, where Louis Saha, Roman Pavlyuchenko and on-loan Emmanuel Adebayor have all left, with Giovani dos Santos almost certain to follow. That leaves Jermain Defoe, who only played a bit-part role last season, and youngster Harry Kane as the only strikers at the club.

This is obviously the major headache for Villas-Boas. Speaking in pre-season, after playing Bale as a makeshift striker, he said: "We are always looking for one more striker, since it's a position that we're looking to strengthen. I think taking three strikers into a Premier League season is more than enough. Sometimes it's not, but hopefully it is. We're trying to bring somebody else in."

But even if AVB manages to bag himself a striker, unearth a new Modric, hit the ground running and restore his reputation after his Chelsea disappointments, finishing in the top four is likely to be beyond Tottenham. Manchester City, Manchester United and Chelsea are expected to take the top three positions, leaving Liverpool, Arsenal, Newcastle and Spurs to battle it out for the scraps.

• Follow me on Twitter @DomRaynorESPN


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