Southend's reward for knocking out Carling Cup holders Manchester United is a trip to Tottenham in the quarter-finals of the competition.
The Shrimpers, who started the day bottom of the Coca-Cola Championship, now face Spurs, who beat Port Vale after extra-time in midweek.
Liverpool will take on Arsenal at Anfield, with the sides also meeting in the Barclays Premiersip at the Emirates Stadium tomorrow.
Newcastle host Chelsea, while League Two side Wycombe are away to Charlton.
The ties will be played in the week beginning December 18.
Southend saw off the Red Devils thanks to Freddy Eastwood's 27th-minute free-kick, and manager Steve Tilson was pleased with the last-eight pairings.
"That is a good draw for us, we've got a couple of players who played for Tottenham, Kevin Maher and Mark Gower, so I'm sure they will be pleased to go back to Spurs," he told Sky Sports.
"Funnily enough I spoke to (Spurs assistant boss) Chris Hughton yesterday and he said that we would be playing them, so it's funny how that's happened.
"We will give it a good go."
Draw for the quarter-finals of the Carling Cup:
Tottenham v Southend
Liverpool v Arsenal
Newcastle v Chelsea
Charlton v Wycombe
Matches to be played week beginning December 18.