Pompey head to National League outfit Harrogate Town looking to avoid an FA Cup upset on Monday.
The first-round encounter has been selected for television coverage on BT Sport, which will add to the pressure on the Blues to come through with the world watching.
The Yorkshire side sit 54 spots below Kenny Jackett’s men in the pyramid and it’s undoubtedly a potential banana skin.
But should the visitors reach round two, the fact the tie is on TV means a lucrative windfall is on offer to the winner.
Each team that comes through in the the FA Cup first round will pick up £36,000 in prize money.
However, sides whose ties are televised also receive an additional FA broadcast fee of £75,000.
Pompey’s first-round clash is one of the four encounters to be shown live on TV.
Dulwich Hamlet v Carlisle, Dover Athletic v Southend and Hayes & Yeading v Oxford will also be broadcast.
It means the Blues, along with the other three winners of televised matches, will pocket a six-figure sum of £111,000 should they manage to progress into the second stage.
That would be a welcome boost for the Fratton Park coffers – especially with the January transfer window approaching.
Not only that, but it would put them a win away from a potential date with a Premier League side in round three.
The prize money then increases as follows for teams that come through second-round ties all the way through to the team crowned winners at Wembley in May:
Second round winners – £54,000
Third round winners – £135,000
Fourth round winners – £180,000
Quarter-final winners – £720,000
Semi-final winners – £1.8m
Semi-final losers – £900,000
Finalist – £1.8m
Winners – £3.6m