Tottenham were dumped out of the Carabao Cup last night – losing 4-3 on penalties to Colchester United.
It’s the first time that Spurs have lost to a Football League side since Mauricio Pochettino took charge in 2014 and first under any manager since losing to Leicester City in 2006.
So where did last night rank in terms of their top-five worst ever defeats under the Argentine?
Here’s what we think.
5. Gent 1-0 Tottenham – February 2017.
Having failed to make it out of their Champions League group with Monaco, Bayer Leverkusen and CSKA Moscow, Spurs were given a second opportunity in Europe, but blew it at the first time of asking. Harry Kane, Dele Alli, Heung Son and Christian Eriksen all featured in Belgium, but Tottenham fell to a 1-0 defeat before a 2-2 draw at Wembley saw them crash out in the Last 32 stage of the Europa League.
4. Stoke City 3-0 Tottenham – May 2015.
Some might have forgotten about this as it came in a difficult first season for Pochettino. It’s actually their second heaviest defeat against a side outside the top-six during his reign. Vlad Chiriches was sent off whilst Jan Vertonghen scored an own goal on what was a horror afternoon at the Bet 65 Stadium.
3. West Brom 1-0 Tottenham – May 2018.
Spurs travelled to the Hawthorns without an away defeat in the Premier League for almost five months, whilst West Brom had just one victory at home since the opening day of the season. Away banker, right? Nope, not with Tottenham. They huffed and puffed before losing out to a last-gasp goal from former midfielder Jake Livermore just to make it that little bit more Tottenham-like.
2. Newcastle United 5-1 Tottenham – May 2016.
Pochettino took his side to already-relegated Newcastle on the final day of the season knowing that a draw would not only secure 2nd place in the Premier League, but a first finish above Arsenal for 21 years. Not only did they not get that point, but they were hammered 5-1 by the 10-man Magpies and finished a point behind their arch rivals.
1. Colchester United 0-0 Tottenham (4-3 on penalties) – September 2019.
Spurs came close to crashing out of the FA Cup to both Newport and Rochdale in 2017/2018, but scored late goals in each before winning the respective replays. But with no second chances in the Carabao Cup, Pochettino’s men were embarrassingly dumped out by the fourth-tier side in a game they were 1/8 to win with some bookies.