Pompey have been drawn away to Premier League side Tottenham Hotspur in the third round of the Emirates FA Cup.
The tie is scheduled to be played during the weekend of January 6-9, with a confirmed date and ticket information to be announced in due course.
It will be the first time that the Blues have visited the impressive Tottenham Hotspur Stadium, which opened in 2019 on the site of the London club's old White Hart Lane ground.
Pompey fans will have fond memories of the most recent FA Cup meeting between the sides.
That took place at Wembley in April 2010, when extra-time goals from Frederic Piquionne and Kevin-Prince Boateng sealed a spot in the final.
Nice! @SpursOfficial v @Pompey @EmiratesFACup 3rd round. #2010 💙 #EmiratesFACup
— David James (@jamosfoundation) November 28, 2022
The three other FA Cup clashes have all ended in victories for Spurs – in 1937, 1967 and 1991.
That latter contest was in the fifth round and Tottenham went on to lift the silverware – a feat they have not managed since.
Danny Cowley's men have already had to see off Hereford and MK Dons to reach this stage of the competition.
Meanwhile, Antonio Conte's outfit currently sit fourth in the Premier League and will be facing AC Milan in the last 16 of the Champions League in the new year.
Emirates FA Cup round three draw |
Preston North End v Huddersfield Town |
Middlesbrough v Brighton & Hove Albion |
Chesterfield v West Bromwich Albion |
Manchester City v Chelsea |
Charlton Athletic or Stockport County v Walsall |
Boreham Wood v Accrington Stanley |
Tottenham Hotspur v POMPEY |
Derby County v Barnsley |
Cardiff City v Leeds United |
Brentford v West Ham United |
AFC Bournemouth v Burnley |
Coventry City v Wrexham |
Norwich City v Blackburn Rovers |
Aston Villa v Stevenage |
Luton Town v Wigan Athletic |
Oxford United v Arsenal |
Fleetwood Town v Queens Park Rangers |
Liverpool v Wolverhampton Wanderers |
Grimsby Town v Burton Albion |
Blackpool v Nottingham Forest |
Dagenham & Redbridge or Gillingham v Leicester City |
Forest Green Rovers v Birmingham City |
Bristol City v Swansea City |
Hartlepool United v Stoke City |
Hull City v Fulham |
Crystal Palace v Southampton |
Millwall v Sheffield United |
Shrewsbury Town v Sunderland |
Sheffield Wednesday v Newcastle United |
Manchester United v Everton |
Reading v Watford |
Ipswich Town v Rotherham United |
*Don't say it, don't say it, don't say it*#Pompey 🆚 Spurs in the FA Cup, you say? 👀 pic.twitter.com/JjOS322ime
— Portsmouth FC (@Pompey) November 28, 2022