It represents only the 11th time the Blues have travelled to a Premier League club in the competition over the last 26 years, consisting of nine different teams.
So here are the previous 10 FA Cup trips to the home of top-flight clubs during that period, spanning from February 1997 to the present day...
1. Chelsea - January 2012
Marko Futacs battles with Chelsea's David Luiz as Michael Appleton''s Pompey side lose 4-0 at Stamford Bridge in the FA Cup Third Round in January 2012. Picture: Barry Zee Photo: Barry Zee
2. Manchester United - March 2008
Sulley Muntari nets Pompey's winner from the penalty spot in their FA Cup quarter-final triumph at Old Trafford in March 2008. Picture: Nick Potts/PA Photo: Nick Potts
3. Manchester United - January 2007
Glen Johnson and Ryan Giggs look on as Gary O'Neil flicks the ball past Park Ji Sun in Pompey's FA Cup Fourth Round 2-1 defeat at Old Trafford in January 2007. Picture: Jonathan Brady Photo: Jonathan Brady
4. Southampton - January 2005
Yakubu celebrates scoring from the penalty spot at Southampton in the FA Cup Fourth Round in January 2005. However, Peter Crouch's last-gasp penalty gave the hosts a 2-1 win. Picture: Ben Radford/Getty Images Photo: Ben Radford