Winstanley, 47, took the job at Chelsea, alongside Lawrence Stewart, back in 2022, but has had little success during his time in West London.
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Cheslea have spent over £1 billion on new players since his arrival and recently posted the worst financial losses in English football history.
According to The Telegraph journalist Matt Law, Tottenham have made checks on Winstanley in their search for a new sporting director.
It’s understood that Winstanley is unlikely to leave Chelsea, however, so Spurs are also looking at Dougie Freedman.
