City are unlikely to see Donovan Ricketts again after immigration officials blocked him from coming back into the country.
Ricketts, whose contract is up at the end of the season, is stuck in Jamaica - and looks to have played his final game at Valley Parade.
The 30-year-old keeper, one of the highest earners in the squad, would also be in breach of contract if he is unable to turn up to work for training.
Ricketts was stopped at Heathrow Airport on Friday as he returned with Omar Daley from international duty.
An official noticed that although he had a valid passport and work permit, Ricketts had not got the necessary stamp in his documentation to meet UK employment laws.
He was promptly refused entry and put back on a plane to New York, where he hoped to get the passport stamped at the British Embassy.
But when City contacted the immigration agency in Sheffield, they were told that Ricketts had not completed the paperwork within the six-month deadline of the work permit being issued - and therefore it was viewed as invalid.
City could have applied for a new work permit but that would have been turned down because his contract is up in three months; Jamaica are outside FIFA's top 70, so he does not meet the international requirements; and he is no longer the club's first-choice goalkeeper.
"We tried everything we could to get Donovan back in but rules are rules," said City boss Stuart McCall.
"I like the fella and I'm disappointed that he's back in Jamaica. I would love him to get back but the longer things go on, it doesn't look good."
Ricketts, who last played for City at Wrexham in January, saw a move to QPR collapse in the transfer window because of work-permit problems.
McCall brought in Scott Loach on loan to replace him and the Watford youngster has appeared in every game since.
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