Pompey have made a flying start to the League One campaign and currently set second following an unbeaten opening six fixtures.
But tonight the quest for points is in the Checkatrade Trophy, as Gillingham head to Fratton Park for the first match in Southern Group A.
The visitors began the season with successive wins over Accrington and Burton, but have not tasted success since.
They exited the Carabao Cup on penalties at Millwall, while the following four league games have yielded a solitary point.
Some context can be given, however, by the fact that they have faced the unbeaten trio of Walsall, Sunderland and Barnsley.
It leaves the Gills 12th at this early stage, as they look to improve on finishing just six points above the drop zone last term.
Both sides qualified from their 2017/18 Checkatrade Trophy group, with the Kent side going out at Oxford in the second round, while the Blues were beaten by Chelsea’s youngsters in the last 16.
It was Gillingham who came out on top in the most recent Fratton contest between the sides, securing a 3-1 victory after Jamal Lowe had given Pompey the lead.
If tonight’s game finishes all square, both sides will collect a point. A penalty shoot-out will then be held, with the victors earning a bonus point.
Pompey are expected to make several changes from the side that convincingly beat Plymouth in the league on Saturday.
Andre Green and Joe Mason could make their debuts for the Blues having recently arrived on loan deals.
Oli Hawkins (hamstring), Anton Walkes (groin) and Jack Whatmough (hamstring) are definitely missing, with Ronan Curtis away on international duty with Republic of Ireland U21s.
Gillingham skipper Gabriel Zakuani is out with a shoulder injury, so recent loan signing Connor Ogilivie could feature.
HEAD TO HEAD
Pompey: 18 wins
Gillingham: 7 wins
At Fratton Park
Pompey: 11 wins
Gillingham: 1 win
Seats can still be secured online here or from the Anson Road ticket office. Please note that only the South Stand Upper and Nelson’s Family Zone are open tonight.
From 5.30pm this evening, tickets will also be available to buy from the matchday ticket office on Frogmore Road or – with cash only – outside the turnstiles.
Supporters collecting tickets from 5.30pm this evening should visit main reception.
Parking in the North Stand car park is priced just £5 for tonight’s game, with spaces allocated on a first come, first served basis.
The Victory Lounge behind the Fratton End will be open for supporters from 5pm.
Supporters in the UK and Ireland can watch the game live – with commentary and graphics – as part of a new service offered by the EFL. It is priced £10 for a match pass.
Domestic subscribers will, as usual, be able to listen to listen to live commentary from Andy Moon and Guy Whittingham by signing into their account and visiting the match centre from 7pm. Please note that subscribers will still need to purchase a match pass in order to watch the game live.
Overseas subscribers and match pass holders can watch the action, with commentary starting from around 10 minutes before kick-off.
ALSO IN THE CHECKATRADE TROPHY
Kick-off 7.45pm unless stated
Forest Green v Cheltenham (7.30pm)
Charlton v AFC Wimbledon
Crawley v Tottenham U21
Colchester v Southampton U21
Luton v Brighton U21
MK Dons v Peterborough
Northampton v Wycombe
Oxford v Fulham U21
Southend v Cambridge
Yeovil v Exeter
Doncaster v Newcastle U21 (7pm)
Oldham v Barnsley (7.30pm)
Burton v Walsall
Carlisle v Morecambe
Grimsby v Notts County
Lincoln v Mansfield
Macclesfield v Blackpool
Rochdale v Bury
Scunthorpe v Wolves U21
Sunderland v Stoke U21
Tranmere v Crewe