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Manga-wise, Kaiba was beaten in two Shadow Games against Yami Yugi, one Shadow Game by Pegasus, and once again defeated by Dark Diva/Aigami in Darkside of Dimensions. Anime-wise, he lost to Yugi in episode 1, lost to Pegasus, and was again defeated by Dartz, resulting in him facing a Penalty Game each time. You could practically count Anubis' loss to Yugi in Pyramid of Light as Kaiba's defeat since Anubis took over his Duel as well.
This is even higher than Yami-Bakura who was only beaten in a Shadow Game 3 times, once against Yugi's group in the pre-DK Monster World mini-arc (replaced by a one-episode Shadow Duel in the DM anime), beaten by Yami Marik in Battle City, and defeated for good by Atem and the rest of the gang in the final Shadow RPG (although, his soul-clone was also beaten in a Duel within the Shadow Game by regular Yugi).
This is even higher than Yami-Bakura who was only beaten in a Shadow Game 3 times, once against Yugi's group in the pre-DK Monster World mini-arc (replaced by a one-episode Shadow Duel in the DM anime), beaten by Yami Marik in Battle City, and defeated for good by Atem and the rest of the gang in the final Shadow RPG (although, his soul-clone was also beaten in a Duel within the Shadow Game by regular Yugi).
