Pompey have been drawn at home to Arsenal in the fifth round of the Emirates FA Cup.
The tie will take place at Fratton Park in the week commencing March 2.
A confirmed date and ticket info will be announced in due course, but fans can click here to register their interest and be among the first to hear confirmed news.
Arsenal booked their place in round five with a 2-0 victory at Bournemouth, courtesy of goals from Bukayo Saka and Eddie Nketiah.
Pompey's assistant manager Joe Gallen said: "We'll be facing a team full of class, who are one of the superpowers of English football.
"Our players will get a chance to test themselves against the very best and it's a tie we can all look forward to."
"Our players will get a chance to test themselves against the very best and it's a tie we can all look forward to."
Arsenal were convincing 5-1 winners when the sides last met in the FA Cup for a quarter-final contest on the south coast in March 2004.
There were also a couple of classic encounters in 1971, with Mike Trebilcock earning the Blues a replay, which the Londoners narrowly came out on top in.
The most recent contests came in the Premier League during the 2009/10 campaign and the Gunners were 4-1 victors in both games.
Mikel Arteta's Arsenal side – who saw off Leeds in round three – sit 10th in the top-flight table and the club are aiming to secure the FA Cup for a record 14th time.
| Emirates FA Cup fifth round draw |
| Sheffield Wednesday v Manchester City |
| Reading or Cardiff City v Sheffield United |
| Chelsea v Shrewsbury Town or Liverpool |
| West Bromwich Albion v Newcastle United or Oxford United |
| Leicester City v Coventry City or Birmingham City |
| Northampton Town or Derby County v Manchester United |
| Southampton or Tottenham Hotspur v Norwich City |
| POMPEY v Arsenal |