The draw for the third round of the Carabao Cup was made on Sunday afternoon, with the likes of Liverpool and Arsenal given tricky encounters.
Manchester City will be looking to clinch the League Cup for a record-equalling eighth time after defeating Aston Villa in last season's final at Wembley Stadium.
Pep Guardiola's charges will begin the defence of their title with a clash at home to either Championship side Bournemouth or Crystal Palace.
Manchester United, who were eliminated by City in the semi-finals, will be away to the winner of the second-round clash between Reading and Luton Town.
Arsenal were handed a tough trip the King Power Stadium against Leicester City while Liverpool will entertain the winner between Bradford City and Lincoln City.
Reading/Luton vs Manchester United
Leyton Orient/Plymouth vs Tottenham Hotspur
Bradford or Lincoln vs Liverpool
Leicester City vs Arsenal
West Brom/Harrogate vs Southampton/Brentford
Wolves/Stoke vs Gillingham/Coventry
Chelsea vs Middlesbrough/Barnsley
Millwal/Cheltenham vs Burnley/Sheffield United
Manchester City vs Bournemouth/Crystal Palace
Bristol City/Northamtpon vs Burton/Aston Villa
Fleetwood Town/Port Vale vs Everton/Salford City
West Ham United/Charlton vs Leeds United/Hull City
