Wycombe were familiar opponents for Pompey during their four-season stay in English football’s basement.
All of their eight previous league meetings took part in that division and were complemented by a couple of cup clashes.
Wanderers have never played above the third tier and bookies do not believe that will change, instead making them one of the favourites for relegation.
Wycombe brought six successive seasons in the fourth tier to an end by securing promotion into League One.
They snatched the final automatic spot by battling from behind to win at Chesterfield in their penultimate fixture.
Wanderers hit 79 league goals over the course of the campaign, with only second-placed Luton scoring more.
Gareth Ainsworth began his managerial career at Adams Park in 2012, having made more than 100 appearances for Wycombe as a player.
He previously turned out for Cambridge, Preston, Lincoln, Port Vale, Wimbledon, Cardiff and QPR and was still lacing up his boots to appear in an EFL Trophy tie just two years ago.
Wycombe have recently signed goalkeeper Ryan Allsop, who played in both of Pompey’s play-off matches against Plymouth after arriving on an emergency loan from Bournemouth in May 2016.
Marcus Bean netted once in six games during a temporary spell at Fratton Park in 2014, while forward Paris Cowan-Hall previously played for the Blues youth team.
HEAD TO HEAD
Pompey: 3 wins
Wycombe: 3 wins
Last Fratton meeting
Pompey 1 (Evans)
Wycombe 2 (Cowan-Hall, Akinfenwa)
FA Cup R1
November 5 2016
Last away meeting
Wycombe 1 (Kashket)
February 4 2017
Best league finish: 6th in Division Two (1994/95)
Nickname: The Chairboys
Distance from Fratton Park: 84.3 miles
Estimated drive time: 1 hour 34 minutes
2018/19 title odds: 66/1
2017/18 League Two: 3rd
2016/17 League Two: 9th
2015/16 League Two: 13th
2014/15 League Two: 4th
2013/14 League Two: 22nd
2012/13 League Two: 15th
2011/12 League One: 21st
2010/11 League Two: 3rd
2009/10 League One: 22nd
2008/09 League Two: 3rd