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Yes, it is legal to bet on multiple outcomes of an event or game. What is the risk? There is minimal risk involved when betting both sides. A user could make an error when placing a wager or the odds could potentially change while making wagers (try to avoid live games).

How to Bet Both Sides for Guaranteed Winnings

betbothsides : how-to-bet-both-sides

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yes, but it depends on the circumstances. Betting on both teams (also called arbitrage betting or middling) can result in the bettor making a profit  regardless of the outcome  by placing one bet per each outcome (and with different betting companies).

Can You Make Money Betting on Both Teams? - Zensports

zensports : blog : can-you-make-money-betting-on-both-teams

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