Five years ago Torquay United were playing in the Conference and reached the final of the FA Trophy, whilst Portsmouth were in the Premiership and won the FA Cup.
Tomorrow at Plainmoor, they face each other as equals in League Two for the first time in over 30 years.
The two sides met each other earlier this season in the Johnstone's Paint Trophy when Pompey won 5-3 on penalties after a goalless draw during the 90 minutes, and they also played each other in the Worthington Cup with Portsmouth winning 3-0 on aggregate.
Their last League meeting came on October 10th 1980, a game that the Gulls won 2-1 with Les Lawrence and Peter Coffill scoring the decisive goals.
Fast forward back to the present day and both sides' respective managers- Alan Knill and Guy Whittingham- are facing different challenges.
Knill, who succeeded Martin Ling in the close season following a spell as interim manager, is looking to arrest a run of five matches without a win-in the face of injuries problems and financial uncertainties.
The former Bury and Scunthorpe manager is currently without a number of senior players, including goalkeeper Michael Poke, last season's Player of the Year Aaron Downes and summer signing Ben Harding.
He currently has four loan players at the club, including central defender Anthony O'Connor, midfielder Jak McCourt and forwards Ade Azeez and Paul McCallum, who made his debut on Tuesday night after joining from West Ham United.
As well as this, he also recruited French midfielder Damien Mozika who played under him at Bury and Scunthorpe on a short term deal.
Like with many clubs in League Two at the moment, money is tight for the Gulls, which reflected the recent decision by the Gulls' board to make three staff redundant, including Club Secretary Kerry Haggan.
However, a good run in the FA Cup, the first round starts on November 9th, could provide the Gulls with some breathing space.
Pompey boss Guy Whittingham is starting a re-building job as they look to climb their way back up the leagues after a financial meltdown, which has seen them relegated three times in as many seasons.
Now under the ownership of their Supporters' Trust, Pompey are currently unbeaten in the current month of October and have reached the Quarter Finals of the Johnstone's Paint Trophy as the re-building process at Fratton Park continues.
