---
title: "The biggest cup upsets of all time"
canonical: "https://readtottenham.com/2019/09/25/the-biggest-cup-upsets-of-all-time/"
type: "post"
language: "en-GB"
author: "Ste Hoare"
section: "Tottenham News"
published: "2019-09-25T08:52:18Z"
modified: "2026-09-22T17:03:34Z"
---

# The biggest cup upsets of all time

Tottenham suffered a shock Carabao Cup shootout defeat to League Two side Colchester United on Tuesday night. Despite naming a strong side, Mauricio Pochettino’s men failed to breakdown the U’s, with the tie going straight to penalties after a goalless 90 minutes. Christian Eriksen and Lucas Moura both missed from the spot, which allowed Colchester defender Tom Lapslie to seal a memorable win for John McGreal’s side. Following Spurs’ dramatic exit, we’ve taken a look at some of the biggest cup upsets of all time.