A CTR filed from the bank to FinCEN is only reported on large amounts, usually >$10,000 but I had one for $3,000 once. Now Casino's will file a W-2G on certain amounts as well. I've had different amounts that triggered W2G's, so I don't know what the hell they use. Slots, Poker, Keno, etc. have lesser amounts than table games and sports bets.
The best way to get around this is to spread the money around in small amounts and/or with multiple people helping you. As far as anonymity, people don't care about anyone walking in a sportsbook. Where a hat and glasses and no one will know the better.