Dunfermline failed to strike a deal for the return of Cardiff City defender Malachi Fagan-Walcott on transfer deadline day.
The former Spurs centre-half spent the second half of last season on loan at East End Park.
And he had previously had an injury-curtailed spell playing under boss James McPake at Dundee.
But McPake was left frustrated after a fresh approach for the 22-year-old was turned down just hours before the window closed.
It is understood Fagan-Walcott was one of two players from south of the border that McPake was keen to sign last week.
But it was instead decided to farm out the youngster to National League side York City, although surprisingly neither club have yet publicly confirmed that move.
After an initially difficult start to life with Dunfermline earlier this year, Fagan-Walcott proved an inspired signing as he helped haul the side out of relegation trouble and to the verge of a promotion play-off spot.
He also assisted with three goals at the other end during his 15 outings with the Fifers.
Target
His cultured displays meant he was a long-term target for McPake this summer.
But the youngster, whose one appearance for Tottenham came in the Champions League, was initially retained by Cardiff during pre-season and for the opening to the new campaign.
He has played three times for the Bluebirds this term, including 90 minutes in last week’s 5-3 defeat to Southampton in the Carabao Cup.
However, it was always likely he would head out on loan to gain more first-team experience.
Dunfermline were optimistic they could persuade Cardiff and the player’s representative that they were the best destination for the promising stopper.
But they were forced to admit defeat in a frustrating final day of the transfer window.
McPake will now turn his focus on the domestic loan market after setting his sights on at least two more new recruits following the capture of Tobi Oluwayemi, Josh Cooper and Tommy Fogarty.
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