Thoi Singh was bought by Chennaiyin FC during the 2015 Hero ISL auction. He completed most tackles (71) by any player in his debut season. 2018-19 turned out to be Thoi's best season at the Marina Machans in terms of attacking returns as he scored four goals and provided one assist. Having already won the Hero ISL trophy twice with Chennaiyin FC, the dynamic midfielder added a runners-up medal during the 2019-20 season with Chennaiyin FC. He continued being an important player in the Chennaiyin FC set-up in the seventh edition of the Hero ISL.
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India