Tottenham fans are openly disheartened by their Premier League start, leading to serious anxiety ahead of their League Cup third-round clash against Liverpool. In the last round, however, Roberto De Zerbi's team thrashed Charlton 5-1, but goalscorers Mikey Moore and Kevin Danso have since gone out on loan.
The situation in the league for the Spurs is grim: no goals scored in four matches, defeats against Brentford and Newcastle, alongside goalless draws with Nottingham Forest and Everton. The upcoming trip to Anfield represents a daunting challenge. From the six thousand travelling fans, only a handful have witnessed their team triumph in Merseyside.
Head-to-head history of Liverpool and Tottenham:
- Total matches: 187
- Liverpool wins: 92
- Draws: 45
- Tottenham wins: 50
Last five meetings between the teams:
- 15 March 2026: Liverpool 1 - 1 Tottenham (PL)
- 20 December 2025: Tottenham 1 - 2 Liverpool (PL)
- 27 April 2025: Liverpool 5 - 1 Tottenham (PL)
- 6 February 2025: Liverpool 4 - 0 Tottenham (League Cup semifinal)
- 8 January 2025: Tottenham 1 - 0 Liverpool (League Cup semifinal)
In their March meeting, the Merseysiders dominated and took the lead through a penalty from Dominik Szoboszlai, but Richarlison's equaliser in the 90th minute secured a crucial point for the Londoners in their relegation battle. This marked the Brazilian's sixth goal against Liverpool. Sadly, he won’t be available for Tuesday’s match, having been suspended and omitted from the season's squad.
That draw was a rare glimmer of hope for the Londoners. Two seasons ago, the teams clashed in the League Cup semifinals. In the first leg in London, Ange Postecoglou's side secured a 1-0 victory thanks to a goal from Lucas Bergvall, who narrowly avoided a red card. However, in the return leg at Anfield, the Reds crushed their opponents 4-0 to reach Wembley.
Tottenham’s winless streak at Anfield is now stretched to 17 matches, with 12 of those ending in defeat. In their last 30 visits to the iconic ground, Spurs have managed only one win—back in the 1998 League Cup under the management of George Graham, during which they went on to lift the trophy.
The lone victory for Tottenham at Anfield in the 21st century came in May 2011, when Harry Redknapp's team triumphed 2-0 against Kenny Dalglish's side, courtesy of goals from Rafael van der Vaart and Luka Modric.
In the last 20 encounters between the two, Liverpool have emerged victorious 14 times, losing just twice. Any positive result for De Zerbi's men on Tuesday would indeed be a sensational turnaround.
