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Wanderers will host Championship outfit Middlesbrough in the Carabao Cup second round in a repeat of the 2004 final.
Ian Evatt’s men beat League Two Barrow 1-0 in the opening round thanks to West Brom loanee Zac Ashworth’s free kick.
Meanwhile, Middlesbrough ran out 3-2 winners at Huddersfield after goals from Samuel Silvera, Isaiah Jones and Riley McGree.
Wanderers are winless in their last 10 matches against the North East club – a run stretching back to April 2013.
The Whites were beaten 2-0 when the sides last met in April 2019, with Ashley Fletcher bagging a brace that day.
The draw was carried out by former Leicester defender Wes Morgan and ex-Aston Villa boss Martin O’Neill.
The competition remains regionalised at this stage, with separate draws taking place for the northern and southern sections.
A number of top flight clubs enter the competition in the second round including the likes of Chelsea and Tottenham.
All second-round fixtures are currently scheduled to take place on Tuesday, August 30 and Wednesday, August 31.
Here is the Carabao Cup second-round draw in full
Northern section
Tranmere Rovers v Leicester City
Salford City v Leeds United
Harrogate Town v Blackburn
Stoke City v Rotherham United
Wrexham v Bradford City
Doncaster Rovers v Everton
Wanderers v Middlesbrough
Port Vale v Crewe Alexandra
Nottingham Forest v Burnley
Sheffield Wednesday v Mansfield Town
Wolverhampton Wanderers v Blackpool
Sheffield United v Lincoln City
Southern section
Bristol City v Queens Park Rangers or Norwich City
Plymouth Argyle v Crystal Palace
Reading v Ipswich Town
Portsmouth v Peterborough United
Luton Town v Gillingham
Swansea City v Bournemouth
Fulham v Tottenham Hotspur
Exeter City v Stevenage
Wycombe Wanderers v Sutton United
Birmingham City v Cardiff City
Newport County v Brentford
Chelsea v Wimbledon
Source