The draw was made on Monday evening by former Magpies manager Ruud Gullit - who took Newcastle to the final in 1999 - and ex-England global Paul Ince.
Ties will take place between January 4-7.
That's right, it's the draw for the third round of the FA Cup, live from Stamford Bridge, home of the current holders.
Woking, one of two non-league sides guaranteed to be in the third round, will host Premier League team Watford.
Newcastle legend Alan Shearer took to Twitter to react, with the tie bringing together two of his former clubs, Shearer won the Premiership with Rovers.
Pompey have lost just once in the league this season, picking up 44 points from a possible 57 in the third tier so far.
Jose Mourinho will be hoping for a good cup run to ease the growing pressure on his shoulders following a poor start to the new season and Man Utd will host Championship outfit Reading at Old Trafford in the third round of the FA Cup.
However, earlier that season Pompey did win 2-0 at Carrow Road when a goal from Dave Kitson in the 73rd minute and a late penalty from Greg Halford, after Leon Barnett was sent off, sealed the win in Norfolk.