Pompey will face Fleetwood three times in nine weeks after drawn against each other in the FA Cup’s third round.
The Blues will visit Fleetwood Town, with ties to be played between Friday, January 3 and Monday, January 6, 2020.
Joey Barton’s side are presently placed seventh in League One, two points ahead of Pompey and with a game in hand.
The teams were meant to meet at Fratton Park in league action last month, only for Barton to postpone the fixture after his squad was weakened by three international call-ups.
That game has been rearranged for March 10 – with the teams already scheduled at Highbury Stadium on February 22.
Now, following this evening’s FA Cup draw, they will also meet at the start of January, ensuring three encounters within a 67-day period.
Strangely enough, the clubs will have gone through 2019 without facing each other, despite operating in the same league.
Their last meeting was December 29, 2018, when Kenny Jackett’s men ran out 5-2 winners at the home of the Cod Army, a result which at the time strengthened their grip at the top of League One.
The reverse fixture took place months earlier at Fratton Park, Oli Hawkins’ goal securing a 1-0 Blues victory in October 2018.
And despite not playing each other in 2019, they will now go head-to-head in the opening three months of 2020.
Meanwhile, it will be a return to a former club for Gareth Evans, who joined Pompey in July 2015 after turning down a new deal at Highbury Stadium.