Tottenham made a comical error involving a contract they had prepared for Luis Diaz before he ultimately chose to join Liverpool at the end of the January transfer window, according to reports. The north Londoners were keen admirers of the 24-year-old, who signed a long-term deal at Anfield last week after Porto accepted a fee of around £37million for his services.
Diaz was identified as a target by Tottenham ahead of the January window after establishing himself as one of Europe's most exciting talents during his time with Porto.
He scored 16 goals for Porto in all competitions between the start of the season and his move to Liverpool after impressing with Colombia at last summer's Copa America.
Tottenham had reportedly been planning to launch a move for Diaz for some time before losing out at the hands of their Merseyside counterparts during the final stages of the January window.
Liverpool were keen on waiting until the summer to firm up their interest in the forward but accelerated their plans to snap him up after learning of Tottenham's desire to act quickly.
The Reds had a deal wrapped up in a matter of days and officially confirmed Diaz's arrival on the eve of deadline day to end the race for his signature.
Tottenham failed in their efforts to sign Luis Diaz last month
Tottenham went on to thrash out two last-minute deals to sign Juventus duo Dejan Kulusevski and Rodrigo Bentancur before the window slammed shut on Monday evening.
They are said to have made a painful mistake in their negotiations with the latter, though, in mixing up his name with that of Diaz amid the chaos of the mid-season market.
Club chiefs were left red-faced after they handed Bentancur's lawyers a contract they had drafted up for Diaz, according to Record Portugal.
It is claimed that the error 'left a lot of people surprised' but did not prevent Bentancur from eventually putting pen to paper on a deal until the summer of 2026.
Tottenham had to work hard to land the Uruguayan midfielder and Kulusevski after missing out on a number of key targets over the course of the January window.
They initially appeared to be the favourites to sign Adama Traore from Wolves before Barcelona muscled in to secure his services on loan with the option to buy at the end of the season.
A move to bring in Aston Villa midfielder Douglas Luiz also proved to be a step too far, according to the Daily Mail, before they went on to fail in their efforts to land Diaz.
However, former Premier League striker Noel Whelan recently suggested that Antonio Conte will be pleased with Tottenham's business in the January market in spite of the club's shortcomings.
"We’ve seen that he’s let a lot of supposedly quality players go from Tottenham because they couldn’t play the way he wanted," Whelan told Football Insider.
"He’s gone for these two, Kulusevski and Bentancur, because he’s familiar with them and he knows what he will get from them.
"He wouldn’t bring them to Tottenham if he didn’t think that they would add some real quality to the side. I still believe they are a few players short, but it’s a step in the right direction.
"Conte will be very happy to get those deals done, it gives Spurs a real platform now to build on in the summer."