Manchester City have failed to sign McDonald Mariga after the Parma midfielder's work permit application was turned down.
A deal was in place to bring the Kenya international to Eastlands but City were undone by permit complications and had an immediate appeal turned down on Monday.
City officials attended a hearing at Wembley which included representatives from both from clubs, the FA, Premier League and the PFA but were told the player did not meet the criteria to play in the country.
Despite having 24 caps for Kenya and playing in at least 75 per cent of their games over the past two years, Mariga is the victim of his country's lowly Fifa ranking of 98.
By letter of the law, the East African country must be in the top 70 before a move to English football can become legitimate, a rule which City look set to dispute.
The club are expected to launch a further appeal, but will not be able to complete the signing before Monday's transfer deadline and may be forced to resurrect the deal in the summer.
A fee of around £7million had been agreed between City and Serie A side Parma, who paid £2million to Swedish side Helsingborgs for his services in 2008.
Mariga is under contract with the club until summer 2012 and has made eight starts in a Parma shirt this season.