With star players Harry Kane and Dele Alli injured, and Son Heung-min away at the Asian Cup with South Korea, it's hardly the ideal time for Tottenham to be facing their great rivals Chelsea.
Worse still that it's the semi-final second leg of the Carabao Cup, with Wembley very much within view, and with a one-goal lead to defend from the first fixture.
It will be a real test of the fortitude of Mauricio Pochettino's team at Stamford Bridge, with Manchester City then lying in wait in the final should they pass it.
Rising star Kazaiah Sterling, 20, is once again likely to be on the Spurs bench, the young striker hoping to make an almighty impact by sending his team to the final.
Sportsmail tells you everything you need to know about Sterling ahead of the crunch match in west London.
How likely is Sterling to be involved?
It was a telltale sign that Sterling was not involved in Spurs' under-23 Premier League International Cup match against Athletic Bilbao on Wednesday night.
Though another striker, Vincent Janssen, started and scored in an extraordinary 5-4 Spurs win as he continues his return from injury, Sterling was not in the squad.
A similar thing happened last Friday in Spurs' International Cup match against Norwich City before Sterling was named on the bench for the Premier League win at Fulham on Sunday afternoon.
So it appears likely that Pochettino will again have Sterling on the bench at Stamford Bridge, probably alongside Fernando Llorente with Lucas Moura potentially starting up front.
If Tottenham find themselves in need of a goal during the latter stages of Thursday night's match, perhaps Pochettino will give Sterling the chance to shine.
Sterling also trained with the first-team at their Enfield base on Wednesday, though he has been involved with Pochettino's senior squad for some time.
Does he have any first-team experience already?
He does. Six minutes to be precise.
Sterling replaced Dele Alli for his first-team debut late in Spurs' 3-0 Champions League group stage win over Cypriot side APOEL Nicosia last season.
Still running on at Wembley Stadium, even in a dead rubber after Spurs had already secured top spot in their group, must have been a thrilling experience.
Indeed, Sterling tweeted afterwards: 'Dream come true making my debut in the @ChampionsLeague tonight and to win.'
Amusingly, Sterling spent some eight minutes on the touchline waiting for the ball to go out of play before he could come on, which couldn't have helped the nerves.
He was also an unused substitute in the Premier League match at Manchester City in April last year but that has been it in terms of competitive senior game time.
Sterling did also catch the eye by scoring in a post-season friendly win over Kitchee in Hong Kong in May 2017.
But Pochettino holds him in high esteem?
Yes, Pochettino name-checked Sterling when discussing potential attacking options amid his ongoing injury crisis ahead of the Fulham match.
The Argentine was making the point that a false nine could be deployed at the spearhead of the attack rather than a conventional centre-forward.
'I was watching Barcelona and the striker was Leo Messi,' Pochettino said. 'You can play Llorente, Dele Alli, [Erik] Lamela; you can play Kazaiah Sterling, Troy Parrott, I don't know.
'It's not that you have to play with one specific striker. We are so crazy, the managers, that sometimes we decide to do something different.'
But Sterling is very much a striker?
Yes, he is most definitely a centre-forward and while he wears the No 54 shirt in the extended Spurs first-team squad, there is nothing false about this 'nine'.
Sterling has a good touch, sound technique, physical strength - he is 5ft 9in but muscular - and a sharp eye for goal as shown by the four goals scored in his last four Under-23 Premier League 2 outings.
In an interview with football.london back in 2017, Sterling said: 'My strengths are running in behind to finish, being aggressive and competing.
'My weakness is probably my play in tight areas, which I can definitely improve on.'
Is there anyone he models his game on?
Sterling revealed in that same interview that he admired Manchester City striker Sergio Aguero, a good example of 'a smaller player who still gets around the pitch a lot.'
But Pochettino has deliberately not sent Sterling out on loan these past couple of years so he can play alongside a certain Harry Kane on the training field and learn the tricks of the trade.
The manager was asked back in March 2017 about his reluctance to loan young players out - as may happen at Chelsea or Manchester City.
He said: 'One example is Kazaiah Sterling. Next season he will be here and it means every day there is an under-18 striker training with Harry Kane. There is no better teacher to learn from.
'Where would we send him? It would be a completely different philosophy. But if you don't have the opportunity to train every day with the first team, it is true that it is good to grow up in another place and come back.
'But here we try to provide the facility to train with the first team for any player who can cope with the pressure.'
It offered an interesting snapshot into the Pochettino philosophy when it comes to bringing young players through and as Kane, Harry Winks and others will testify, Spurs is among the best clubs for progression from the academy.
As Sterling himself said: 'Harry Kane is the perfect inspiration. He's come through the academy as well. That's the standard I'm trying to hit.'
So if Sterling has not been loaned out, what experience does he have?
Certain schools of thought would argue that a 20-year-old probably should have 20-30 Football League matches under their belt by now having gone out somewhere on loan.
Tottenham's policy means that Sterling's career has been exclusively in the Under-23 Premier League competitions and, before that, the FA Youth Cup and UEFA Youth League.
In the academy games he has featured in, Sterling has performed well. He was the club's leading scorer in the Premier League 2 during 2017-18, with eight goals in 20 appearances.
Also last season, when still eligible for the under-19 Youth League, he found the net against Real Madrid and twice against Borussia Dortmund in the continental tournament.
In a see-saw match against Real, played at Tottenham's training ground, they found themselves under serious second-half pressure but Sterling's clinical finish from a Marcus Edwards pass late on secured a 3-2 win.
Sterling, who attended Winchmore School in north London, and joined Spurs from Leyton Orient, has gradually worked his way through the ranks.
He has also demonstrated a good deal of mental strength to recover from injury setbacks that could have slowed his development.
In the youth side, he was involved in Tottenham's run to the semi-finals in 2014-15, scoring in a 2-0 win over Chelsea in the first leg of the semi-final. But Chelsea roared back to win the second leg 5-2.
The two London rivals met again at that stage in 2017 with Sterling netting his fourth goal of their Youth Cup run in the first leg. Chelsea, though, thrashed Spurs 7-1 in the second leg to reach another final.
Two years on and this bright talent could well be facing Chelsea again - but in very different circumstances.