Ipswich will be without Connor Wickham for the start of the new season, while David Norris has also sustained an injury.
Teenage striker Wickham took a knock in pre-season training for the Tractor Boys on Monday and could be out until September, according to the team's medical staff.
It comes as a blow to the club, with the 17-year-old regarded as one of the club's brightest young talents and a prospect for national honours in the future.
"I took a shot at goal and felt my ankle give way," Wickham told the club's official website.
"It's very frustrating and it looks like I will be out for six weeks."
Norris is also struggling to be fit and will miss the upcoming friendlies against Leiston and Bury, with manager Roy Keane worried whether he would play any part in a further pre-season fixture against West Ham.
"Chuck (Norris) is a concern for us as well. He's got a stiff back and you have to be careful with that type of problem," Keane said.
"He won't play over the next few days and will be touch and go for the West Ham game at the weekend."