Tottenham Hotspur

Sold for £10m, now better than Skipp: Levy made a mistake with Spurs’ 5 ft 10 flop – opinion

This erstwhile Lilywhite holds all the tools to flourish in Ange Postecoglou’s system.

Ange Postecoglou will be delighted with Tottenham Hotspur’s start to the 2023/24 Premier League campaign, but he will know of the rocky road still to traverse ahead of what could be a momentous crescendo to a new chapter.

Few anticipated the London team’s spectacular seasonal ascent following such a difficult and disappointing 2022–2023 season, which saw Antonio Conte fired for the fourth time in as many years at Tottenham Hotspur Stadium.

Nevertheless, Tottenham is set for a successful year despite the loss of star striker Harry Kane, as they have risen to a two-point, table-topping lead in the Premier League after ten games.

Postecoglou’s plans have been strengthened by a number of intriguing additions, but Kane wasn’t the only player to depart; Harry Winks also left Spurs after a long career to join relegated Leicester City for a £10 million fee.

Harry Winks: Premier League seasons
Season Apps Starts Goals Assists
21/22 19 9 0 1
20/21 15 9 0 0
19/20 31 26 0 0
18/19 26 17 1 0
17/18 16 9 0 1
16/17 21 3 1 1
Stats via WhoScored.

Skipp is a solid squad option even though he has played well for Tottenham this season as a substitute. He doesn’t, however, seem to be getting a big part under Postecoglou anytime soon.

To be fair, Winks’ circumstances are probably similar to those of Postecoglou, and the 27-year-old would likely feel let down given his reluctance to change his fluid starting lineup unless absolutely necessary.

That doesn’t mean he wouldn’t have performed well in a pinch, though, and with Spurs in dire need of a central midfielder, holding onto the dependable passer might have made sense.

Regretfully, he is currently leading Leicester in an incredible campaign, and it looks likely that they will be promoted soon.

Harry Winks’ style of play

Perhaps Postecoglou could have found a use for Winks, and perhaps chairman Daniel Levy should have held off on the sale, especially when considering the player’s innate passing prowess; simple but effective, he could have been a sturdy metronomic presence to add depth to an aspiring team.

As per FBref, Winks ranks among the top 1% of midfielders across divisions similar to the Championship for pass completion and passes attempted, the top 24% for progressive passes and the top 23% for progressive carries per 90.


He is, undoubtedly, one of the second tier’s superlative ball-playing specialists, and his infusion with Enzo Maresca’s system at the King Power Stadium has been absolutely magnificent.

Harry Winks’ season at Leicester in numbers

His delightful curling strike against beleaguered Queens Park Rangers last weekend rubber-stamped his stature as the division’s leading midfielder this season, though not without merit.

Having started 14 league matches this term, Winks, aged 27, has completed a mega 95% of his passes, made 5.4 ball recoveries per game and succeeded with 67% of his attempted dribbles, as per Sofascore.

In summary, Winks’ ability to perform at a level higher than Leicester’s current standing is abundantly evident; however, the Foxes are making an unstoppable push back to the top, and the former Spurs star will likely continue to be their center of attention following their promotion.

The technical skill of the ten-cap England international would have been ideal for Tottenham’s new system, as Postecoglou put an emphasis on dominance through precise, composed passing football. The style of play would have been fast-paced and fluid.


James Maddison, Pape Sarr, and Yves Bissouma have created a strong triumvirate in the middle of the park, and it’s evident at this point that the Tottenham manager prefers to stick with the same starting lineup, or very close to it, in order to preserve intensity and coherence.

Even so, Winks would have been a great choice because he brought a unique skill set that was ideal for the new look. Maybe if the new manager had had more time to work with him, the two styles would have blended together nicely.

Oliver Skipp was still preferred to provide a hardworking middle-man alternative, but he was in fact sold.

How Oliver Skipp compares to Harry Winks

Although Skipp is still only 23 years old and has proven to be a reliable backup option over the past few years, the decision to let Winks go has raised some doubts, especially in light of the Leicester player’s performances this season.

Like Winks, the midfielder who earns £40,000 a week is a calm passer who finishes in the top 18% of midfielders in Europe’s top five leagues for pass completion and the top 27% for tackles per ninety.

Even though he is four years younger than the other player, Skipp doesn’t seem like he will be improving to match Tottenham’s increasing level of playmaking.


As per Sofascore, the 23-year-old completed 87% of his passes across 23 Premier League matches last year – worse than Winks this season.

What the media have said about Oliver Skipp

Despite the numbers above, talkSPORT pundit Perry Groves was left criticising his lack of positivity, claiming that, alongside Pierre Emile Hojbjerg, Spurs have a “double appendix” that “don’t do anything.”

It’s probably justified, then, that Hojbjerg has only started once in the top flight this season – harsh, but the table speaks for itself and it’s hardly a good argument to build against Postecoglou, who is thriving at the helm.

Reporter Alex Crook said in less critical terms that Spurs need Skipp “not good enough” if they are to succeed, although the Australian manager seems to agree as he has only started one Premier League game this season.

Though nothing came of it in the end, and the public will never know if this was due to a lack of interest, Tottenham was rumored to have been willing to cash in on their academy graduate in the summer.

It’s possible that Winks’ sale indicated a reluctance to thin the crop excessively, but given that Football Transfers’ valuation model values Skipp at £24 million, it’s impossible to avoid wondering if the wrong man was let go.


Although Skipp has performed well this season for Tottenham coming off the bench, he is a respectable squad option. However, it doesn’t appear that he will be securing a significant role under Postecoglou anytime soon.

To be fair, Winks’ situation is probably similar to Postecoglou’s, and the 27-year-old would probably be left feeling disappointed considering his unwillingness to alter his free-flowing starting lineup unless forced to.

However, that doesn’t mean he wouldn’t have performed well when needed, and considering Spurs’ need for a central midfielder, it might have made sense to hang onto the reliable passer.

Unfortunately, he is currently leading Leicester in a fantastic campaign, and a date with promotion appears likely.

increasingly likely; to say that Spurs may rue his sale might be a bit of a stretch, but Winks would undoubtedly play a part and given the unlikely title charge, squad depth really is imperative when reaching the business end.

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