Mauro Rosales will have to stay at Ajax until the end of the season, after River Plate failed to finalise a deal on Friday.
The forward is eager to return to his native Argentina and River had been keen to push through a deal.
The Argentinian transfer window did not close until Friday, but River failed to come forward with a suitable package and Ajax have revealed their disappointment with the events of the last couple of weeks.
"Until Friday, the KNVB were keen to cooperate on the outward transfer," Ajax technical director Martin van Geel told Het Parool. "The Argentinian market is open two weeks longer than ours, but now the transfer window is closed and Rosales stays."
Ajax coach Henk ten Cate added: "It's especially very sad for Rosales himself. For weeks that boy has been hurled to and fro. He lived between hope and fear.
"One day he thinks that he goes back, the next day he hears something different again."