English League Cup holders Tottenham will start their defence of the trophy in the third round against Newcastle.
Juande Ramos's side, who beat Chelsea in last season's final, travel to St James' Park in search of their first win over Newcastle since December 2005.
Chelsea visit Portsmouth, who have already lost 4-0 at Stamford Bridge, as Luiz Felipe Scolari's team try to get back to the Wembley final.
Manchester United take on Middlesbrough at old Trafford. Arsenal will take on Sheffield United at the Emirates in a repeat of last season's fourth-round clash.
Everton, who were beaten in the last four by Chelsea, will travel to face Blackburn. Rafa Benitez's Liverpool host Crewe.