Maurizio Sarri began his Chelsea reign by putting together an 18-match unbeaten streak in all competitions, but there are now doubts about how long the Italian will last at Stamford Bridge due to issues on and off the pitch.
Chelsea have recorded 20 points from their last 12 games in the Premier League, but four defeats have left the Blues just three points ahead of Arsenal and Manchester United in the race for fourth place.
The latest setback - a 2-0 defeat at Arsenal on Saturday evening - was followed by Sarri questioning the desire of his players in the media, and it comes at a time when the futures of a number of their most valued players remain up in the air.
Sarri must attempt to focus on the short term with a February date at Wembley Stadium at stake, but there is little doubting that Chelsea have lost their way over the past two months and the pressure is growing on the recently-appointed head coach.
The team's style of play is being criticised by the club's supporters, but Sarri is unlikely to change his philosophy despite Chelsea potentially needing at least two goals to progress through to the final of this competition.
The West Londoners have not scored more than two times against Premier League opposition since October 28, and Sarri is seemingly pinning his hopes on improving that return with the addition of Juventus forward Gonzalo Higuain.
The Argentine must sign before midday on Wednesday to be available for the game on Thursday night, and his presence may prove to be the difference when Chelsea go in search of the goals which they require to get past Spurs.
Sarri still has other quality players at his disposal, but a perception has been generated which suggests that Chelsea need a change and the arrival of Higuain may just act as the catalyst for better results in the coming weeks.
Recent form: WWWL
Recent form (all competitions): WDWLWL
Spurs find themselves in control of third spot in the Premier League standings as they look to earn a place in next season's Champions League, but Pochettino is aware that he is under pressure to deliver silverware.
There will be the temptation to rest players for either the game with Chelsea or Sunday's FA Cup tie at Crystal Palace, but the Argentine will be desperate to end the club's wait for a trophy.
Holding a lead ahead of the visit to Stamford Bridge has given Spurs the edge ahead of Thursday's fixture, but Pochettino will acknowledge that the tie is far from over given the limitations with his squad.
The absence of Son Heung-min, Kane and probably Dele Alli is a significant blow, although this is a squad which has only failed to score in two games - against Manchester City and Manchester United - all season.
Spurs have also won each of their last three showdowns with Chelsea, and that is something which will only provide this group of players with confidence when they take to the pitch on Thursday evening.
Pochettino will believe that a clean sheet can be recorded at Stamford Bridge with Spurs having conceded just five goals in seven matches, three of which came in the December capitulation against Wolverhampton Wanderers.
The boss of the North London outfit will also point to the fact that his side have only overcome Premier League opposition to reach this stage of the competition, despite numerous changes being made for the ties against Watford, West Ham United and Arsenal.
Fewer alterations will be made for their next outing, but this is the first of four games in nine days and Pochettino will be doing all that he can to progress without the need for extra time.
Recent form: DWWW
Recent form (all competitions): LWWWLW
Sarri is likely to make mass changes for Sunday's FA Cup tie with Sheffield Wednesday, meaning that many of the players who featured against Arsenal should start on Thursday night.
Alli is still being assessed by Spurs' medical staff, but the Englishman is unlikely to be risked by Pochettino due to the club's upcoming schedule.
Chelsea possible starting lineup:
Arrizabalaga; Azpilicueta, Rudiger, Luiz, Alonso; Kante, Jorginho, Kovacic; Pedro, Giroud, Hazard
Tottenham Hotspur possible starting lineup:
Lloris; Alderweireld, Sanchez, Vertonghen; Trippier, Dier, Winks, Davies; Eriksen, Lamela, Llorente
Head To Head
Thursday's encounter will represent the 163rd competitive meeting between the two clubs, with Chelsea registering 68 wins in comparison to 54 victories for Spurs.
Chelsea once held a dominant record over Spurs, but the Blues have won just four of the last 11 contests during a period stretching back to the start of 2015.
Spurs have prevailed on five occasions, while Pochettino has also witnessed his side emerge victorious in four of the last half-a-dozen clashes.
We say: Chelsea 1-2 Tottenham Hotspur
Spurs' squad - especially in attack - is being stretched to the limit, but we are backing Pochettino's side to get the better of their city rivals, with Chelsea having struggled for goals since the end of October.