The 29-year-old has played just four games for the season and not since the Magpies' 30-point win over Essendon in round five.
He was expected to be unavailable for a fortnight after the minor operation following that match but missed the Pies' round six win over the Bulldogs, was rested during last week's bye and has already been ruled out of Friday night's blockbuster against Geelong.
He is now expected to also miss the round nine clash with Adelaide on May 22 and return the following week against West Coast at the MCG.
"He'll definitely miss this week and it's unlikely he'll play the following week," Collingwood football operations manager Geoff Walsh told afl.com.au on Wednesday.
"From then on we're thinking that we'll get him up for round 10 where he would be able to get up and go.
"That's what our assessment is currently but we'll monitor that every few days but that's what we're thinking at the moment; round 10 when we play the Eagles."
Jolly's absence against Geelong will see 48-gamer Cameron Wood make his third appearance for the season against the in-form Brad Ottens, who was rested in the second half of the Cats' win over North Melbourne last Saturday.
The Magpies expect to name both captain Nick Maxwell and midfielder Ben Johnson for Friday night but a final decision will be made after training on Thursday.
Maxwell (leg soreness) completed just the warm up of Tuesday's training session at Gosch's Paddock while Johnson (back spasms) was restricted to running laps.
"If [Maxwell] trains [on Thursday] in our last session before selection and he gets through, we'll name him and expect him to play," Walsh said.
"The same will go for Ben as well."
The news is better for defender Chris Tarrant, who completed Tuesday's hit-out and is expected to come in to face the Cats after being a late withdrawal from the Pies' last match; the win over the Bulldogs.
"He trained okay on Tuesday and did everything the doctors wanted him to do," Walsh said.
"He's been in this morning (Wednesday) and he's pulled up well, and we expect him to get through training again on Thursday and he'll be named."
