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Tottenham’s move for Sporting Lisbon's Pedro Porro is in serious doubt, with Spurs believing that the Portuguese club have reneged on a deal for the full-back - despite them agreeing to meet his full asking price.
Tottenham believe a deal worth around £40million had been agreed and were preparing to welcome Porro to Hotspur Way for a medical on Monday.
There is limited time to salvage the move before Tuesday’s 11pm transfer deadline but, given how close they came to a deal, Spurs are expected to resume talks with Sporting.
Porro, 23, is pushing to join the London club and is said to be distraught by the latest developments, having been told by Sporting president Frederico Varandas that he could leave after Saturday's Portuguese League Cup final against Porto.
Spurs have been locked in talks with Sporting for most of January over the defender, with negotiations centred around the schedule of the payments.
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Sporting had lined up former Arsenal full-back Hector Bellerin as a replacement but his loan move from Barcelona is also now in doubt.
Spurs are not thought to be working on any other deals for the first team as it stands, so missing out on Porro would leave them with just one addition this month - Arnaut Danjuma, who joined on loan from Villarreal last week and scored on his debut in Saturday's 3-0 win over Preston in the FA Cup fourth round.
Antonio Conte, the Spurs head coach, has made a new right wing-back a top priority, despite already having Emerson Royal, Matt Doherty and Djed Spence in the squad.
Conte also wants a top centre-half and Bayer Leverkusen's Piero Hincapie is on Spurs' radar, although any move is likely to wait until the summer.