In regards to chess specifically, and playing it of course with no gambling, this is a fiqhi matter, where our esteemed Maraji' have different verdicts.
For example, A.U. Seyid Sistani (may Allah prolong his life) says that it is absolutely haram.
As for A.U. Seyid Khamenei (may Allah prolong his life), he says if it is commonly seen in the custom of people ('urf) as a gambling instrument, then it is haram, and if not, then it is halal.
You must refer to your Marja' taqleed for this fatwa.
If there was really no risk of loosing in "matched betting", you would have seen all wealthy companies investing in it. Matched betting is a type of calculated betting which means it is a type of gambling with small percentage of risk. It is a betting and betting is not allowed in Islam.
Yes this practice is considered as gambling. In general any practice which involves a prize achieved from the property of the participants is gambling.
Books on Islam, Muslims, Prophet Muhammad(s), Ahlul Bayt.
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