Tottenham's season is undoubtedly approaching a season-defining period. 

A desperately disappointing 1-0 loss at Championship side Sheffield United saw the north Londoners crash out of the FA Cup, before defeat by the same scoreline at Wolves less than 72 hours later allowed Liverpool to move within three points of their top-four rivals. 

Those results mean that Wednesday night's Champions League last-16 second-leg encounter against Milan has taken on even more significance as Antonio Conte's men look to turn a one-goal deficit on its head. 

Speaking exclusively to BT Sport, Glenn Hoddle is under no illusions about the magnitude of the fixture, but admits that the team's best chance this term of claiming an elusive trophy has already passed them by following their FA Cup elimination, which was even more galling given the open nature of the draw. 


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"It was a crushing blow [to lose to Sheff Utd] because it’s the only realistic trophy they could've won. 

"I don't know why they didn't play their strongest side they could possibly play to be honest, and it's a blow for every Spurs fan out there, but that's history.

"Not getting through against Sheffield [United]… if you lose away to Liverpool or Man United, that's a bit different than going to Sheffield United and I think that's piled on the pressure for the Milan game.

"Now you're going into this game where, if you get knocked out of that, there's no trophy coming to Tottenham again this season and if you want to keep your best players, you're going to have to be successful. 

"Getting top four would be successful to a degree – but it's not going to keep players at the club, not like Kane or maybe even Son.

"They want to be associated with winning things, so I think it was a massive blow and a big mistake really not to play your best XI.

"Yes, Sheffield United could still knock [their best XI] out, but it knocks on the pressure for the Milan game."

Son Heung-min and Harry Kane during Tottenham's defeat at Manchester City in January
Glenn Hoddle suggests that Son Heung-min and Harry Kane may leave Tottenham if they don't win the Champions League this season

Having the second leg against the Rossoneri back in England undoubtedly brings some psychological comfort, but Hoddle believes a relentlessly attacking approach from the outset would be unwise. 

"Any game in the Champions League, if you have that philosophy, you'll get turned over.

"It makes it slightly easier nowadays without the away goals [going into the second leg], because you would always be on the back foot thinking: 'If they get an away goal, we are stuffed.'

"But [the new rule] allows you to go [for it] at a certain time in the game if you're still one goal down.

"This isn't a top, top Milan [team] of yesteryear, but it's still a very good side and the tie is so balanced.

"Even if we score a goal five minutes from the end, it doesn't matter. If you keep a clean sheet – which is the most important thing – you fancy Tottenham to score at some stage, even if it was five minutes to go.

"Then you throw the kitchen sink at it with a view [that]: 'If it goes to extra time, it’s at our manor', rather than having to do that in Milan. If you're 3-0 down, that's a different story. 

"For Tottenham, an early goal would be fantastic because it sets the stadium alight, it settles everyone down and it poses a little question to them, so at the moment they've got something to defend and hang onto.

"The [Spurs] players will be totally up for this. They'll be a different animal at Tottenham. I think the atmosphere will make the players play at a quicker tempo.

"When they play like that – which they did against Man City, and Chelsea in the second half – they're a decent side."

On that point, Hoddle is keen to counter the idea that Conte is an exceptionally defensively minded coach. 

"Yeah, he sets the team up to get behind the ball, but you're not a defensive team if you've scored 46 goals in the Premier League," he points out. "We're fourth behind Arsenal, Man City and Liverpool [in that respect]. 

"If they were on 26 goals, I could understand Tottenham fans saying: 'It's too defensive, I don't like the way he plays', but we've ended up scoring 46 goals [so far].

"We've probably let too many in, funnily enough. [Conte] won't be happy with the goals they've let in. It's a very strange story, Tottenham's season at the moment. It's like Forrest Gump: 'Life's like a box of chocolates.'

"With Tottenham, you really don't know what you’re going to get. They turn up and you think: 'Wow, they're on it today.'

"The next game, you think: 'It's not the same team – all their brothers are playing today!' It's a different team. It's a big, big game for the club."

Hoddle certainly felt Conte's side can take a great deal of heart from the first leg at San Siro.

"First half, Spurs went one goal down, but they dominated the game. [They] didn't have enough in the last third, which I think they will have at home.

"There was nothing there really for me to be fearing. You've got to stop the crosses if Giroud's playing - that's something Spurs will have to do well - but they're not a team that's going to come and dictate the play and take the ball away from Tottenham.

"I think they'll look to defend stoutly, be hard to break down and look to break.

"Leao is probably their threat on the break. He's got pace, he's got strength. If they get the ball up to Giroud and he sets things up, they could be a danger."

And a prediction? "I'm going for a 2-0 win. We'll get a clean sheet and go through."

That just so happens to be the result that Chelsea secured back in England after falling behind against Borussia Dortmund at Signal Iduna Park. 

Mirroring that comeback would be the perfect tonic to a campaign that has threatened to turn sour. 

Watch coverage of Tottenham's Champions League last-16 second leg against Milan exclusively live on BT Sport 1 and BT Sport Ultimate from 7pm.