The left-back had been in solid form with Mauricio Pochetitno's team in recent weeks.
However, he is set to miss their game on Monday against Newcastle United due to injury.
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Chilwell, who has only played 18 games this season, will be seeking specialist opinions.
Manager Mauricio Pochettino told reporters: "We need to wait until he sees the specialist.
I cannot go in advance. I hope it's not a big issue but in this moment after eight or nine months with the club, I prefer to be cautious and wait."
The latest setback is thought to be a knee injury, while his previous issues related to his hamstrings.