But even its simpler iterations often go against bookmakers’ terms and conditions, so it is generally considered fraudulent. However, it involves exploiting signup and other bonus offers, so betting operators do their best to stop it.ĭepending on how it’s conducted, matched betting can fall anywhere from a gray area to completely illegal. Matched betting involves strategically placing bets on an event in a way that allows one to win no matter the result, while taking advantage of free bet offers.īecause you’ve covered all possible outcomes, matched betting does not involve gambling but math.