Pompey have been drawn at home to Southern League Premier Division South side Harrow Borough in the first round of the Emirates FA Cup.
The tie – which sees the sides meet competitively for the first time – will take place at Fratton Park on the weekend of November 5-8.
The visitors have already had to negotiate four qualifying rounds to reach this stage of the competition.
They shocked the latter side from the National League South by battling from behind to win 4-2 on home soil at Earlsmead Stadium on Saturday, courtesy of James Ewington's hat-trick and an Imran Uche strike.
It meant that the Reds would compete in the FA Cup first round proper for just the fifth time in the club's history.
Harrow are currently sitting 10th in their division, with five wins and the same number of defeats from their 10 fixtures.
| Emirates FA Cup first round draw |
| Bradford City v Exeter City |
| Sunderland v Mansfield Town |
| Hayes & Yeading United v Sutton United |
| Sheffield Wednesday v Plymouth Argyle |
| Dagenham & Redbridge v Salford City |
| Carlisle United v Horsham |
| Dover Athletic or Yate Town v Yeovil Town |
| Scunthorpe United v Doncaster Rovers |
| Rotherham United v Bromley |
| POMPEY v Harrow Borough |
| Gillingham v Cheltenham Town |
| Morecambe v Newport County |
| Banbury United v Barrow |
| Fleetwood Town v Burton Albion |
| AFC Sudbury v Colchester United |
| Northampton Town v Cambridge United |
| St Albans City v Forest Green Rovers |
| Stratford Town v Shrewsbury Town |
| FC Halifax Town v Maidenhead United |
| Chesterfield v Southend United |
| Rochdale v Notts County |
| Kidderminster Harriers v Grimsby Town |
| Wigan Athletic v Solihull Moors |
| Boreham Wood v Eastleigh |
| York City v Buxton |
| Ipswich Town v Oldham Athletic |
| AFC Wimbledon v Guiseley |
| Harrogate Town v Wrexham |
| Hartlepool United v Wycombe Wanderers |
| King's Lynn Town v Walsall |
| Crewe Alexandra v Swindon Town |
| Bolton Wanderers v Stockport County |
| Charlton Athletic v Havant & Waterlooville |
| Oxford United v Bristol Rovers |
| Crawley Town v Tranmere Rovers |
| Leyton Orient v Ebbsfleet United |
| Milton Keynes Dons v Stevenage |
| Lincoln City v Bowers & Pitsea |
| Port Vale v Accrington Stanley |
| Gateshead v Altrincham |