The West Yorkshire club - who have won just once in the last nine games - were already due to be without prop Craig Kopczak.
However, they have now seen winger Mason Caton-Brown drop out of their 19-man squad as they seek the win needed to ease fears of being dragged into the relegation mire.
Chester explained: “Mason got a whack in the face (against Castleford Tigers last week) and has some (concussion) symptoms.
“I’m probably looking towards Rocky (Hampshire) going to the wing.
“Max Jowitt will come in and play full-back this week and we’ll probably put Rocky out there.
“We have the option of putting Bill Tupou out there and bringing Joe Arundel into centre but I’m a bit reluctant to do that.
“I’m leaning towards Rocky on the wing.”
Half-back Hampshire - who started his career at Wigan - has been Wakefield’s main full-back this term but has experience of playing on the wing during a prolific loan spell with Castleford in 2016.
Jowitt has scored six tries in nine games for Trinity this season but has been injured with a broken thumb and not played since the 25-18 Magic Weekend loss against Catalans Dragons on May 25.
On Kopczak’s injury, Chester added: “It’s just a leg problem.
“He took a really bad cork last weekend. He got it early on but managed to play the rest of the game.
“He’s missing and we’ll have to make that change with Mason so it means we lose another two again.
“But Danny Kirmond’s back out on the training field and we should get him back next week.”