Pompey have been drawn away to League Two side Stevenage in the first round of the Carabao Cup.
The tie – which will likely be played behind closed doors – is scheduled to take place at Broadhall Way on the weekend of September 5/6, although teams can mutually agree to a change of date.
Former Blues skipper Paul Merson conducted the draw, which was shown live on Sky Sports News.
But Alex Revell's outfit were granted a reprieve when a points deduction saw Macclesfield relegated to the National League instead.
The first ever competitive meeting between the sides came at this stage of the competition back in August 2010.
Pompey won 2-1 that evening, with Nadir Ciftci and Michael Brown scoring the goals for Steve Cotterill's visitors.
The Blues reached the third round of last season's Carabao Cup, while Stevenage fell at the first hurdle.
|Carabao Cup Round One – South|
|Bristol City v Exeter City|
|Plymouth Argyle v Queens Park Rangers|
|Swindon Town v Charlton Athletic|
|Forest Green Rovers v Leyton Orient|
|Milton Keynes Dons v Coventry City|
|Crawley Town v Millwall|
|Stevenage v POMPEY|
|Peterborough United v Cheltenham Town|
|Brentford v Wycombe Wanderers|
|Northampton Town v Cardiff City|
|Luton Town v Norwich City|
|Birmingham City v Cambridge United|
|Newport County v Swansea City|
|Oxford United v AFC Wimbledon|
|Reading v Colchester United|
|Gillingham v Southend United|
|Ipswich Town v Bristol Rovers|
|Carabao Cup Round One – North|
|Tranmere Rovers v Harrogate Town|
|Crewe Alexandra v Lincoln City|
|Walsall v Sheffield Wednesday|
|Rochdale v Huddersfield Town|
|Preston North End v Mansfield Town|
|Bolton Wanderers v Bradford City|
|Blackburn Rovers v Doncaster Rovers|
|Stoke City v Blackpool|
|Fleetwood Town v Wigan Athletic|
|Grimsby Town v Morecambe|
|Middlesbrough v Shrewsbury Town|
|Derby County v Barrow|
|Scunthorpe United v Port Vale|
|Sunderland v Hull City|
|Burton Albion v Accrington Stanley|
|Salford City v Rotherham United|
|Barnsley v Nottingham Forest|
|Oldham Athletic v Carlisle United|