Mounir El Hamdaoui's transfer from Ajax to Fiorentina collapsed on deadline day after the Dutch club demanded a bank guarantee for the payment.
The 27-year-old passed a medical at the Florence club on Saturday, and had announced on Twitter that he was in Italy to finalise the deal on Tuesday.
But with just hours of the transfer window remaining the deal was off after the Italian club could not provide Ajax with proof of funds.
A statement from Fiorentina stated: "Fiorentina announce that it has not been possible to complete the purchase of Mounir El Hamdaoui from Ajax Amsterdam because, after the negotiations had been concluded successfully both with the player and the club, the Dutch club just minutes before the end of the transfer window asked a bank guarantee to the payment, when there was no time to obtain one, in contravention of common practice followed by all major European football clubs."
Meanwhile, Ajax failed with a transfer deadline day swoop for Heerenveen forward Luciano Narsingh, according to the player's agent.
The 21-year-old's representative, Mino Raiola, claims the Godenzonen only made their interest in the player known on Monday.
He told Voetbal International: "It was too short notice. Therefore we ended it.
"Ajax only made their interest for Narsingh known on Monday. He did not want to decide within a day and he has a cup game against Vitesse to play on Tuesday.
"We haven't talked with Ajax about anything. Luciano is very happy at Heerenveen and wants to decide on his future some months from now."
Reports in Holland suggest Ajax also looked into signing Dutch winger Eljero Elia on loan from Juventus.
However, the former FC Twente player has already featured for Juve and on loan at Hamburg this season and is not eligible to play for a third club under FIFA rules.