Felipe Scolari will face Portsmouth away in his first Carling Cup match following the third round draw made today (Saturday).
The match at Fratton Park against the FA Cup holders will played on Tuesday 23 or Wednesday 24 September.
The club comprehensively beaten on the first day of the season have been drawn in this competition twice in the past.
In Chelsea's first season in the League Cup in 1960, a 1-0 defeat at Fratton Park ended our campaign after Millwall, Workington and Doncaster had been overcome.
Then in 1990, after a 0-0 draw at Stamford Bridge, Chelsea won a dramatic third round replay, fighting back to take the game right at the death.
Portsmouth took a 2-0 lead by the break but David Lee pulled one back on 81 minutes, Dennis Wise scored from the spot and then half-time sub Kerry Dixon put Kevin Wilson through for an injury-time winner.
In other third round ties drawn today, there are all-Premier League matches between Blackburn and Everton, Man United v Middlesbrough and holders Spurs must go to Newcastle.
The full draw is:
Arsenal v Sheffield UnitedBrighton v Man City v Derby
Burnley v Fulham
Portsmouth v Chelsea
Blackburn v Everton
Rotherham v Southampton
Swansea v Cardiff
Ipswich v Wigan
Stoke v Reading
Leeds v Hartlepool
Watford v West Ham
Man United v Middlesbrough
Liverpool v Crewe
Aston Villa v QPR
Sunderland v Northampton
Newcastle v Spurs
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