Harry Redknapp has admitted Luka Modric, Rafael van der Vaart and Gareth Bale are all struggling to be fit for Tuesday's European clash with AC Milan.
Bale has not played for Tottenham for three weeks thanks to a back injury, Van der Vaart has a calf problem and Modric is still recovering from an operation to remove his appendix earlier this month.
The key trio will miss Saturday's Premier League match at Sunderland and Redknapp is not sure they will be ready for the first leg of the UEFA Champions League tie against Milan next week.
"They are all struggling at the moment. It's difficult to say whether they'll be fit for Tuesday," said the Spurs boss.
"Luka has started jogging but isn't available tomorrow. Rafa has a calf strain and Gareth is coming back slowly.
"We have one or two injuries but hopefully it won't be too long."
Redknapp has a further headache ahead of the visit to Sunderland after Wilson Palacios made the long journey from London to Honduras to take part in his country's friendly against Ecuador on Thursday.
Redknapp is not happy that the midfielder, who has been struggling with a knee injury, was forced to make the trip for the match.
"International week is a nightmare," said Redknapp.
"Wilson played last week when we weren't sure whether he'd be fit and now he has had to go and play in a friendly game all the way to Honduras.
"I'm not sure of the flight time but it's horrendous."
Redknapp maintains that the match against Milan will stay at the back of his mind until after this weekend's encounter with Sunderland.
Much of the attention on the club has centred on their failed bid for the Olympic Stadium, as well as the glamour tie with Milan at the San Siro.
But Redknapp is keen to throw the focus back on Saturday's game in the knowledge that Manchester City's Champions League hopes could be hit in their derby with United.
A victory will also see Tottenham move ahead of Chelsea, who play Fulham on Monday, and Redknapp has called on his team to build on last week's win over Bolton by recording their third straight triumph.
He said: "Tomorrow is a key game for us. It's the one you worry about.
"We are bang in the frame with the top four and are looking to do our best to keep up there so the league games are all important to us.
"Focusing on Sunderland shouldn't be difficult because the players know the importance of it.
"We have picked up six good points recently and the results last week have put us right into the group again.
"There is nothing between the teams pushing for that fourth spot. We have to focus on that now. That's the key thing."
Tottenham fans have been treated to some entertaining Champions League matches in their first season in the competition - most notably the two games against Inter Milan - and the experience has left Redknapp hungry for more.
"If we got back into the Champions League again it would be great for us," Redknapp said.
"We have had a great run, we have loved every minute of it and we want some more."