Sven-Goran Eriksson's unbeaten Manchester City side have been handed a tricky away tie against Bristol City in the second round of the Carling Cup.
Eriksson's City have made an impressive start
The Robins thrashed Brentford 3-0 in the first round on Tuesday.
Leeds will take on Premier League side Portsmouth, while Nottingham Forest and Leicester will get the chance to reignite their longstanding rivalry.
Bristol Rovers will take on West Ham, while Aston Villa travel to Wrexham and Newcastle host Barnsley.
Cup holders Chelsea are among the top Premiership clubs not yet included in the draw because of their involvement in Europe.
Man City have made an impressive start to the Premiership under former England boss Eriksson, with two wins out of two.
Shortly after his appointment at Eastlands, Eriksson suggested he might be setting his sights on the Carling Cup with a view to ending City's long wait for a major trophy.
Boro won the tournament in 2004 under present England coach Steve McLaren.
"I remember what it was like when Middlesbrough won the Carling Cup," he said.
"I took over a team in Italy that hadn't won anything in 25, 30 years. That was Lazio. So when our first trophy was the Italian Cup people go crazy, like we had won the World Cup.
"When Middlesbrough won the Carling Cup it was like that too."
The ties are scheduled to be played in the week starting 27 August.
Carling Cup second round draw:
Plymouth v Doncaster
Southend v Watford
Nottingham Forest v Leicester
Wigan v Hull
Birmingham v Hereford
Carlisle v Coventry
Bristol Rovers v West Ham
Derby County v Blackpool
Rochdale v Norwich City
Portsmouth v Leeds
Cardiff v Leyton Orient
MK Dons v Sheffield Utd
Burnley v Oldham
Swansea v Reading
Peterborough v West Brom
Shrewsbury v Fulham
Wolves v Morecambe
Middlesbrough v Northampton
Sheffield Wed v Hartlepool
Luton v Sunderland
Wrexham v Aston Villa
Charlton v Stockport
Newcastle v Barnsley
Bristol City v Manchester City
(Ties to be played week commencing 27 August)