Pompey have been drawn away to Harrogate Town in the first round of the Emirates FA Cup.
The tie will take place at Wetherby Road on the weekend of November 8-11. A confirmed date and ticket information is to be announced in due course.
It will be the first meeting between the sides, with the hosts currently sitting eighth in the National League.
But Craig MacGillivray will certainly be familar with the Yorkshire outfit, having made 90 Conference North appearances for them between 2012 and 2014.
They reached this round of the competition with a 2-1 win at Halifax in the fourth qualifying round on Saturday.
Pompey assistant manager Joe Gallen said: "We'll have a bit of homework to do and will try to find out as much as we can about them.
"The FA Cup is a brilliant competition and this is a tie that we'll certainly look forward to."
"It's a side that I've never come up against before, but they're doing well in the National League and it will no doubt be a tough game.
"The FA Cup is a brilliant competition and this is a tie that we'll certainly look forward to when it comes around."
One team have already booked their place in the second round, with Chichester City – the lowest ranked side remaining – receiving a bye due to Bury's EFL expulsion.
|Emirates FA Cup first round draw|
|Ipswich Town v Lincoln City|
|Oxford City v Solihull Moors|
|Crawley Town v Scunthorpe United|
|Harrogate Town v POMPEY|
|Colchester United v Coventry City|
|Sunderland v Gillingham|
|Dulwich Hamlet v Carlisle United|
|Bolton Wanderers v Plymouth Argyle|
|York City v Altrincham|
|Chesterfield or Wrexham v Rochdale|
|Maidstone United v Torquay United|
|Leyton Orient v Maldon & Tiptree|
|Chippenham Town v Northampton Town|
|Haringey Borough or Yeovil Town v Hartlepool United|
|Cambridge United v Exeter City|
|Whitby Town or Stourbridge v Welling United or Eastleigh|
|Salford City v Burton Albion|
|Forest Green Rovers v Sutton United or Billericay Town|
|Bristol Rovers v Bromley|
|Ebbsfleet United or Woking v Notts County|
|Walsall v Darlington|
|Nantwich Town v AFC Fylde|
|AFC Wimbledon v Doncaster Rovers|
|Hayes & Yeading United or Poole Town v Oxford United|
|Shrewsbury Town v Bradford City|
|Grimsby Town v Newport County|
|Gateshead v Oldham Athletic|
|Mansfield Town v Chorley|
|Dover Athletic v Southend United|
|Tranmere Rovers v Wycombe Wanderers|
|Carshalton Athletic v Boston United|
|Cheltenham Town v Swindon Town|
|Accrington Stanley v Crewe Alexandra|
|Potters Bar Town or Barnet v Fleetwood Town|
|Macclesfield Town v Kingstonian|
|Maidenhead United or Wealdstone v Rotherham United|
|Blackpool v Morecambe|
|MK Dons v Port Vale|
|Stevenage v Peterborough United|