the ritual could only be used once every sixty years, and it was never successfully completed in two centuries. To put into perspective how costly this was.
The squabbling between the seven started the Holy Grail Wars and cost everyone their chance to make their wish. The original Einzbern ritual required seven mages working in unison to complete the Heaven's Feel. Arguably a larger, overarching theme across the different incarnations of the Holy Grail War.Several of the others have their Loophole Abuse come back to hurt them pretty badly, the worst easily being Kayneth, who made his fiancee his servant's prana source so he wouldn't need to use his own, but in the process she fell in love with said servant and made her a target, ultimately getting them both killed. He doesn't win, but he makes it through the war alive and is the only one of the surviving Masters who is better off at the end of the war than he was at the start. Waver Velvet is the only Master in Fate/Zero who doesn't cheat at some point through the Fourth Holy Grail War.When Shobu is about to win, Benny claims that his sister is sick and that he needs to remain undefeated so that he can pay for her treatments, but Mimi tells Shobu he is lying and he finishes him off. Shobu figures it out and manages to confuse him and get an advantage, then Mimi destroys the cameras. Benny Haha uses cameras to spy on the cards in Shobu's hand and predict his moves.In their second duel, he tries to hypnotize Shobu so he'll fall asleep and lose by default.
In their first duel, Jamira swaps his shuffled deck with a pre-arranged deck that he knows the order of so he'll always get good draws. He tries to blast Frieza from the stands as revenge, but Zeno immediately erases him from existence for attempting to break the rules. In the Tournament of Power, he is angered that he was tricked and eliminated by Frieza, and humiliated when Frieza calls him an amateur/second-rate dilettante. However, Vegeta says there is no need to disqualify him, and proceeds to defeat Frost himself, humiliating him. Goku is allowed back in the tournament and Frost is disqualified. During the Tournament of Destroyers, he is caught having cheated against Goku and Piccolo with a poison needle. Dragon Ball Super has Frost, the Universe 6 version of Frieza. Ikki's abusive family repeatedly tried to sabotage his matches with tactics like imprisoning and poisoning him shortly before the matches, but he would overcome this and win anyway. Ayase ultimately loses because her guilt dulled her reflexes and skills. Ikki actually reports her cheating before the match but persuades them to let the match continue as he wanted to prove a point. When Ayase is scheduled to have a tournament sword fight with Ikki, she first tricks Ikki into using his Ittou Shura (a technique he can only use once a day due to Heroic RRoD) before the match, then litters the battlefield with dozens of magical traps (you're allowed to use traps, but you have to set them up during the match, not before it). He's called in to the office and forced to take a test to prove that he'd legitimately earned his scores, and when he tries to use his ability on the proctor, he gets found out. This catches up with him after Nao catches him in the act repeatedly. In Charlotte, Yu uses his ability to transfer his soul to another person to look at their answers on the test. 
The only time the cheater isn't punished is when Mitsuya suffers a thumbing and knocks his opponent out faster than the referee can call out the foul (and yes, the referee had noticed the foul-Mitsuya was just faster at punching out his opponent).
In All Rounder Meguru, the referees are extremely observant and ready to punish a foul. One of the marks of Akagi's brilliance is his ability to cheat really well.
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