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 Premiersip at the Emirates Stadium on Sunday.
Newcastle host Chelsea, while League Two side Wycombe are away to Charlton.
Southend saw off the Red Devils thanks to Freddy Eastwood's 27th-minute free-kick, and manager Steve Tilson was pleased with the draw.
"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 on Friday and he said that we would be playing them, so it's funny how that's happened.
"We will give it a good go."