The transfers of Tottenham players Mido Ahmed and Hossam Ghaly to Birmingham look to have fallen through.
"You could say that both deals have been stuttering a bit," Birmingham manager Steve Bruce said on Thursday. "But the Mido one is a million miles away from happening."
Birmingham agreed to pay ?6 million for Mido on July 20, dependent on personal terms. Mido's Egypt teammate, Ghaly, was also set to join the newly promoted club.
"There are a few issues," Bruce said. "It is a big blow and I have felt better. It looks as if we are really struggling with the Mido deal and I might have to look elsewhere. As for Ghaly, it is faltering a little but I am still hopeful of reviving that deal. I haven't given up hope."
Middlesbrough signed defender Luke Young from Charlton on Thursday on a four-year deal worth ?2.5 million.
The 28-year-old Young, who has played seven games for England, will be the third player to join Middlesbrough this offseason.
He joins striker Tuncay Sanli and forward Jeremie Aliadiere, while defender Jonathan Woodgate converted his loan deal from Real Madrid into a permanent transfer.
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