Barnsley will have to do something they have not done this century if they are to progress to the fifth round of the FA Cup - win at Fratton Park.
The Reds who reached the fourth round for the first time in seven years with a 3-1 win at Crewe have failed to win any of their last six trips to the South Coast since Craig Hignett, Bruce Dyer and an Adrian Whitbread own goal earned the Reds a 3-1 win in March 1999, losing four.
The two sides have only ever met once before in the FA Cup, and it was their first ever meeting 113 years ago, Barnsley winning 1-0 at Oakwell in the second round in 1907.
Portsmouth - who were beaten in the League One play-offs last season as Barnsley secured automatic promotion - have had to win three ties to get to this point, winning 2-1 at Harrogate, 2-1 against Altrincham and 2-1 at Fleetwood. They did reach the fourth round last season but were knocked out in a replay by QPR and are aiming to reach the fifth round for the first time since 2009-2010 when they were runners-up in the competition, losing to Chelsea in the final.