Reports have suggested that he will definitely need one, but in fact Glenn Roeder still retains a small amount of hope it could be avoided and a final decision has not yet been made.
And there could be good news this week for Paolo, who has only played in one friendly game, as well.
"Steve had seven weeks off and within 10 or 12 days he got a little bit of a mystery injury with pain in his shin," says Glenn.
"He has had a couple of weeks' rest now, and it very possible that if the pain reappears this week when he starts training he will have a minor operation which would keep him out for two or three weeks.
"That would be a great shame for him - and a great shame for us.
"But we will have to wait and see; Steve left us very fit at the end of last season and he was in the form of his life in terms of what he was producing for the team.
"We do have a couple of injuries but everyone, none more so than Manchester United, a team with probably the biggest squad in the Premiership, seems to be carrying a few.
"All clubs seems to have picked up a few over the summer, and it is par for the course at this time of the year.
"We have two players who are going to miss the game, and we always knew Don Hutchison wasn't going to be fit for the start of the season.
"But I would have liked Paolo Di Canio fit for the start of the season and I certainly would have liked Steve Lomas fit for the start.
"In Paolo's case, he could easily be fit and in full training for the beginning of the week, the fact of the matter is he has not played too much football in the last four months because he was injured against Charlton.
"He worked so hard in the summer to come back on the 18th of July fully fit - which he did - and then he played very well in those 65 minutes against Southend.
"Then he has got a small injury in training and it has taken a little bit longer than anticipated to recover.
"We have had him scanned on a number of occasions in the last 12 days and we fully expect him to be back in training by the middle to the end of next week.
"He is keeping himself fit in the gym, and we know he is not a person who needs a lot of work with the football to regain his touch because he has got such natural ability, and hopefully now he is not going to be out for more than 10 or 12 days.
"I suppose we have no more injuries than any other club and we have to live with it; that is why you need strength in depth.
"Maybe, funnily enough, it is just in the striking department where we haven't and if I was allowed to make one more signing that is the area I would like to strengthen."
One broadsheet newspaper gave West Ham's team selection for Monday as having Vladimir Labant in the middle of midfield, while claiming Christian Dailly would play left back at the expense of Nigel Winterburn.
Seasoned West Ham followers may have other views about Glenn's first line up of the season - where the main choices are who to put in as the 'fourth' midfielder alongside Trevor Sinclair, Joe Cole, and Michael Carrick, and who plays at right back.
Grant McCann does not make the trip as he has been called up on international duty with Northern Ireland for Wednesday's game with Cyprus.
Congratulations to youngster Phil Lumsden, who travelled with the first team party for the first time.
SQUAD: James, Van der Gouw, Pearce, Repka, Dailly, Breen, Winterburn, Cole, Cisse, Carrick, Johnson, Sinclair, Kanoute, Defoe, Labant, Camara, Moncur, Garcia, Sofiane, Forde, Lumsden.