Mauricio Pochettino has been frequently praised for the job which he has done at the North London outfit, but the Argentine remains tasked with ending the club's lengthy period without any silverware.
Pochettino's opposite number Maurizio Sarri finds himself in a similar position having never won a trophy as the senior man in the dugout, and it leaves the duo eager to earn a place against either Manchester City or Burton Albion in February's final.
Here, Sports Mole selects its strongest combined XI from both squads, using only players available for Tuesday's match.
Neither Hugo Lloris nor Kepa Arrizabalaga have been totally convincing between the sticks this season, but we are siding with the young Spaniard at Chelsea. The 24-year-old is under pressure to justify a huge transfer fee and seven-year contract, but the former Athletic Bilbao stopper has conceded just 17 times in 27 appearances.
Kieran Trippier has failed to build on his fine World Cup campaign with England, so Cesar Azpilicueta gets the nod with us at right-back. Neither Ben Davies nor Marcos Alonso have been particularly impressive on the opposite side of the backline, but with Chelsea supporters starting to call for Emerson Palmieri to be given a chance in the top flight, Davies edges out the Spaniard.
There have been question marks raised over the performances of both Antonio Rudiger and David Luiz in the centre of Chelsea's defence, but we cannot ignore the fact that the West Londoners have shipped just 16 goals in 21 Premier League outings so we are picking the latter to partner Toby Alderweireld. Jan Vertonghen and Davinson Sanchez have both spent time out of the Spurs team, so Alderweireld is the logical selection alongside Chelsea's flamboyant Brazilian.
N'Golo Kante has been used in a more advanced position by Sarri this season, but with Spurs missing Eric Dier and Victor Wanyama, we feel inclined to start the ball-winner as our holding midfielder. That would give Christian Eriksen and Dele Alli licence to take on more creative roles either side of Kante, with the pair having impressed in recent weeks.
Eden Hazard is an obvious pick with 10 goals and nine assists coming from 20 appearances in the Premier League during the current campaign, and Son Heung-min has played himself into the team with a remarkable return of eight goals and five assists from just six outings in all competitions.
The selection for the head of the attack is equally simple. Alvaro Morata netted twice for Chelsea against Nottingham Forest at the weekend, but Harry Kane naturally gets our vote. The England skipper has contributed a goal or assist in each of his last eight appearances in all competitions and has netted 19 times in total this season.