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Match betting is not 100% illegal, however many crypto casinos/sportsbook might accuse you fraud, void the bet and you will have problems when withdrawing the money.
Soon or later the crypto casino/sportsbook will know when you place a "Free Bet" on casino A then you place a "Lay Bet" on other casino.
And when there is an issue with your account because of the matched betting, not all crypto casino will return your deposit/free bet and not all crypto casinos allowed Italian users to play on their platform (depend on the casino license).
Im not saying that matched betting is a crime and you will get trouble with crypto casinos, its just a friendly reminder so you must research more about crypto casino first before doing that.
Ok, and how can bookie prove that he is doing match betting?
Today bookies can accuse for anything and take your money, cancel bets, etc as in their t&c is stated that they can do whatever they want.
I am doing this for more than 15 years and I could write a book about sportsbooks, bonus hunting, arbing, value betting, courtsiding, etc.
There are various methods, and one of them is:
All of the sportsbook operators have a software to track odds and betting pattern from all sportsbook providers.
It can detects a potential arbing opportunity from the odds discrepancy and it can monitor suspected account/individual who places bets on both sides across different bookmakers.
Big winnings and Big loses, bet amounts on the same match, bets on certain odds, time etc by ordinary users will be monitored too.
Etc.
How many casino/sportsbooks in this world? Thousands, or even Millions? Yes
How many of the main sportsbooks provider in this world? hundreds? Nah, far less than that.
Is it hard for them to detects it with all of the data they have? Nope
You have done this for more than 15 years, you should know better than me.