Pompey have lost their past four games in all competitions and haven’t won in the league since Shrewsbury’s visit to Fratton Park on August 17.
The head coach made five changes to his side for the 2-1 defeat at the hands of Cambridge United on Saturday.
And he’ll be tempted to make more, along with a formation change, as he looks to get Pompey out of their current rut which also includes one goal in four League One outings.
The system switch could see him look to use wing-backs, making the most of the impressive Mahlon Romeo’s skills set, and go head-to-head with Plymouth boss Ryan Lowe’s preferred way of playing.
But what does that mean in terms of the starting XI?
Well, it could mean the likes of Marcus Harness, Ellis Harrison and Shaun Williams miss out, while Kieron Freeman, John Marquis and Louis Thompson are handed starts.
Here’s an example of how Pompey in a 3-5-2 system for tonight’s game could look.
1. Goalkeeper - Gavin Bazunu
The keeper had no chance with Cambridge United's opener on Saturday but will no doubt feel he could have prevented Liam O'Neill's and the U's' second goal from the edge of the penalty area. His distribution is key to setting up Pompey attacks. On Saturday, he recorded a 100-per-cent success rate from 43 passes completed. It will be vital again tonight as Pompey bid to stay on the front foot against the Pilgrims.
2. Centre-back 1 - Kieron Freeman
Was dropped for the game against Cambridge United, following his substitution against MK Dons. But with Pompey struggling to create chances and a change in formation a real possibility for the visit of Plymouth, the former Sheffield United man could benefit. A right-sided role in a back three would suit him. And with the 29-year-old used to over-lapping centre-backs during his time with the Blades, he could still pose a threat moving forward.
3. Centre-back 2 - Paul Downing
Downing was criticised for failing to prevent Joe Ironside from heading home Cambridge's opener on Saturday and was later substituted as the Blues chased the game. Yet a lot of the criticism was unjustified as he was a calming influence at the back. With Pompey eager for a greater presence going forward tonight, his presence along with an additional central-defensive partner could be key for any counter-attacks.
4. Centre-back 3 - Sean Raggett
Danny Cowley is aware that Pompey are not at their most fluid when a right-footer plays on the left at the back. But he has no other option at the moment because of injuries to Clark Robertson and Connor Ogilvie. Raggett has played there for the majority of his time at Fratton Park and can be relied on defensively. Has been one of Pompey's stand-out performers this season and his presence will be vital against Luke Jephcott.