David Weir, Kirk Broadfoot and Kris Commons have been ruled out of Scotland's clash with Holland.
Broadfoot missed Rangers' draw against Hearts on Saturday as he struggles to shake off foot and calf problems.
Veteran defender Weir has also been forced to miss the trip to Amsterdam after picking up a knee knock.
Derby County midfielder Commons has failed to recover from a calf injury which has sidelined him for the last month.
It remains uncertain if the trio will recover in time for the World Cup qualifier with Iceland next Wednesday.
Scotland boss George Burley has drafted in Rangers full-back Steven Whittaker to help provide cover for the absences of Weir and Broadfoot.
Burley is also sweating over the fitness of captain Barry Ferguson and vice-skipper Stephen McManus after they both missed training on Tuesday.
Scotland assistant manager Terry Butcher concedes McManus is unlikely to be fit for the trip to Holland, but is hopeful he could be back for the Iceland encounter.
"McManus has got a swollen ankle. It's improving day by day but we don't think he'll play on Saturday, he is doubtful," said Butcher.
"We are optimistic about his chances for the Iceland game."
Butcher is more optimistic over Ferguson's fitness for the Dutch test.
"Barry had X-rays today and we are waiting on the results. He wants to play and will train tomorrow if the results are good," added Butcher.
"If medical evidence puts him in danger then he won't play but, as far as
we're concerned, he feels fine and it looks positive."