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Andy Robertson is about to make Tottenham ask an uncomfortable Destiny Udogie question

Chelsea v Tottenham Hotspur - Premier League
Chelsea v Tottenham Hotspur - Premier League | Jacques Feeney/Offside/GettyImages

It took Andy Robertson a couple of games to get going, but he ended up being one of the standouts for Tottenham Hotspur at the end of the preseason, showing that quality of crossing and overall two way ability at left back that made him such a key target for Spurs going back to the winter transfer window when he only didn't leave Liverpool for Tottenham then as Kostas Tsimikas would not be able to return to Anfield from Roma.

Robertson is 32 years old and admittedly on the last legs of his career, looking finished over the last year as Liverpool replaced him with young Hungarian international Milos Kerkez at left back. But Tottenham not only wanted Robbo for his leadership, but they also believed that he still had something left in the tank. And it's always telling when Roberto De Zerbi gives the OK to a deal that was already in the works.

Tottenham have an interesting situation developing at the left back position. They just sold Djed Spence to Serie A giants Inter Milan after the World Cup standout for England requested a transfer to a Champions League club, and Souza is still expected to leave on loan for more minutes.

Destiny Udogie needs to watch his back

That means Tottenham Hotspur are left with Destiny Udogie and Andy Robertson as their two left back options. Udogie is the unequivocal starter right now and another Italian international whom Roberto De Zerbi is a big fan of.

It's easy to see why De Zerbi likes Udogie. When he is at his best, he is the top option not only at Tottenham but also one of the best left backs in the Premier League. He is great at progressing play, one of the best left backs in the world at pure passing of the ball from a technical stand point, and a great athlete who was legitimately not far off from Djed Spence in terms of defensive quality.

the problem with Destiny Udogie is that the former Udinese man is difficult to trust with all the injuries he has suffered, and after a bout of several injuries last season, he did not look good at all upon his return under De Zerbi, struggling with basic defensive actions.

Robertson can put real pressure on Udogie this season if the latter is not fully fit, and going into ther 2026/27 Premier League season, there are already serious questions about Udogie's ability to make it through the season. It wasn't long ago when Robbo was regarded as the best left back in the Premier League, and Tottenham fans aren't going to count him out from surprising them.

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