Pompey have been drawn at home to AFC Wimbleon in the first round of the Carabao Cup.
The two League One sides will meet at Fratton Park in the week beginning August 13.
Pompey won both meetings between the teams last season, triumphing 2-0 at Kingsmeadow and 2-1 on home soil.
There have been no previous cup clashes with the Dons in their current guise.
The Blues were drawn against the old Wimbledon in the League Cup on four occasions, however, and only managed to progress once.
Pompey suffered an extra-time defeat to Cardiff in the first round of last season's competition, although drawn ties this year will go straight to penalties.
It was a similar story for Neal Ardley's Londonders, who were beaten after 120 minutes by Brentford.
A confirmed date for the tie and ticket information will be announced in due course.
|Carabao Cup Round One – Southern Section|
|Millwall v Gillingham|
|POMPEY v AFC Wimbledon|
|Cheltenham Town v Colchester United|
|Yeovil Town v Aston Villa|
|Southend United v Brentford|
|Reading v Birmingham City|
|Wycombe Wanderers v Northampton Town|
|Swindon Town v Forest Green Rovers|
|Norwich City v Stevenage|
|Exeter City v Ipswch Town|
|Milton Keynes Dons v Charlton Athletic|
|West Bromwich Albion v Luton Town|
|Bristol Rovers v Crawley Town|
|Bristol City v Plymouth Argyle|
|Cambridge United v Newport County|
|Queens Park Rangers v Peterborough United|
|Oxford United v Coventry City|
|Carabao Cup Round One – Northern Section|
|Rotherham United v Wigan Athletic|
|Tranmere Rovers v Walsall|
|Crewe Alexandra v Fleetwood Town|
|Scunthorpe United v Doncaster Rovers|
|Macclesfield Town v Bradford City|
|Grimsby Town v Rochdale|
|Sheffield United v Hull City|
|Nottingham Forest v Bury|
|Middlesbrough v Notts County|
|Sunderland v Sheffield Wednesday|
|Leeds United v Bolton Wanderers|
|Carlisle United v Blackburn Rovers|
|Mansfield Town v Accrington Stanley|
|Port Vale v Lincoln City|
|Preston North End v Morecambe|
|Oldham Athletic v Derby County|
|Shrewsbury Town v Burton Albion|
|Blackpool v Barnsley|