Town have drawn Stevenage at home in the first round of the Capital One Cup. The League Two club are now managed by former England striker Teddy Sheringham.
The sides last met in the competition two seasons ago when Boro ran out 2-0 winners at Broadhall Way, the only time the teams have previously faced one another in competitive action.
First round ties will be played during the week commencing 10th August with Town's game almost certainly on the Tuesday evening.
Last year the Blues exited at the first hurdle, losing 1-0 away at Crawley Town after extra-time. It was the ninth time the Blues had been knocked out of the competition by a side from a lower division in 12 seasons. Manager Mick McCarthy is yet to win a cup tie since taking over as Town boss.
The Blues' best recent performance in the competition was reaching the semi-finals in 2010/11 when they were defeated by Arsenal.
Town will learn their Championship fixtures for the 2015/16 campaign at 9am tomorrow when they will be available on TWTD.
Meanwhile, former Town striker Frank Nouble has joined Chinese club Tianjin Songjiang on a two-year deal following his release by Coventry.
Ex-Town centre-half Gareth McAuley has signed a new one-year contract with West Brom.
Capital One Cup - First Round
Carlisle United v Chesterfield
Nottingham Forest v Walsall
Fleetwood Town v Hartlepool United
Scunthorpe United v Barnsley
Bolton Wanderers v Burton Albion
Accrington Stanley v Hull City
Rochdale v Coventry City
Oldham Athletic v Middlesbrough
Huddersfield Town v Notts County
Blackburn Rovers v Shrewsbury Town
Morecambe v Sheffield United
Doncaster Rovers v Leeds United
Wigan Athletic v Bury
Northampton Town v Blackpool
Sheffield Wednesday v Mansfield Town
Rotherham United v Cambridge United
Crewe Alexandra v Preston North End
York City v Bradford City
Port Vale v Burnley
Peterborough United v Crawley Town
Yeovil Town v Queens Park Rangers
Plymouth Argyle v Gillingham
Swindon Town v Exeter City
Bristol Rovers v Birmingham City
Ipswich Town v Stevenage
Luton Town v Bristol City
Charlton Athletic v Dagenham & Redbridge
Wolverhampton Wanderers v Newport County
Brentford v Oxford United
Portsmouth v Derby County
Southend United v Brighton & Hove Albion
Milton Keynes Dons v Leyton Orient
Cardiff City v AFC Wimbledon
Millwall v Barnet
Wycombe Wanderers v Fulham
Colchester United v Reading