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- Ichigo in Bleach practically lives by this trope. He confronts Byakuya three times total during the Soul Society arc, once in the beginning, where he's effortlessly defeated, another time on the bridge, where Yoruichi takes him away, and even though he put up a better showing it was all but outright stated he would be destroyed, and finally fought him atop Sokyoku Hill, where he managed to pull a victory. He even invoked this trope again in his three confrontations with Grimmjow, and one can argue this case for Ulquiorra as well, having their first confrontation shortly before Ichigo's last fight with Grimmjow, which Ulquiorra easily dispatched Ichigo by stabbing a hole in his throat (luckily Orihime was there to heal him), then again in the hall in which even his Vizard form couldn't do anything, and finally defeating him when his Superpowered Evil Side takes a stronger form before Ulquiorra could kill Uryu and Orihime.
- Count Aizen in. Ichigo loses to him in Soul Society (first), then in fake Karakura town where he suffered heroic BSOD (second), and finally 3rd round when Ichigo unleashes his newly found powers which shock and scares Aizen off beyond belief.
- Speaking off Grimmjow, he was interrupted twice before he could use his release on Ichigo during their third fight.
- One Piece had Luffy confronting Crocodile a total of three times, doing better but still getting defeated upon the first two, before finally pulling a victory the last time in the ruins.
- Shinn Asuka's initial confrontations against Kira in Mobile Suit Gundam Seed Destiny play out like this. The first time Kira effortlessly disables him in one slash, the second Shinn freaks him out by dodging a few of his attacks (Kira had up until that point flawlessly one shotted everyone who crossed his path thus far) before Athrun takes over, although it was clear Shinn would have still lost, and finally in their third battle Shinn has prepared extensively and exploiting a flaw in Kira's fighting style, takes him down although Kira survives. They actually fight a few more times after this but always to a draw as Shinn's new machine is unable to exploit the earlier flaw but he's still grown in skill to the point where Kira can't get a hit on him.
- Happens twice in Bakuman。, with the main characters' attempts to get a popular manga that will allow Mashiro's fiancee Miho Azuki to get a lead role. Their first series gets canceled and they quit their second under the condition that if they can't get something serialized by the time their contract ends, they can no longer write for Jump. They have three chances to do so, and fail the first two, but their final manga, Perfect Crime Party, manages to get serialized but this gets subverted when it turns out that PCP won't be able to get a sponsor for an anime.
- Muhyo has three separate encounters with Enchu. In the first at the MLS, Enchu leaves after Muhyo sentences the ghosts he sent. In the second at the Arcanum, he escapes with Rio, before her traitor's mark can be removed. In the third, Muhyo is able to bring Enchu to his senses and convince him to drive out Teeki from his body.
- Between Magical Girl Lyrical Nanoha A's, and Magical Girl Lyrical Nanoha StrikerS, it took Fate three tries to pass her Enforcer exam. It is implied that some of her difficulty came from taking the test during the period in which Nanoha was recovering from her wounds (thus causing Fate emotional distress), and it is pointed out that as the pass rate is 15%, and Chrono also failed the test once, this is still fairly good, especially considering Fate passed "with flying colors" the third time.
- In Mai-Otome, Arika and Nina have three battles after Nina's Face–Heel Turn. The first two end with no clear winner, but Arika is victorious in the third.
- In the Battle Frontier, Ash fought the seventh and last Frontier Brain, Brandon, three times, and finally defeated him the last time.
- Diamond and Pearl, Dawn wants to catch a Buneary from the very beginning. Two Buneary foil her battles. The third one just happened to fall madly in love with Ash's Pikachu.
- Also in DP, Dawn's Contest losing streak ended with her victory in the Wallace Cup, her third endeavor.
- In Dragon Ball, Goku wins the Strongest Under the Heavens Tournament on his third try (against Piccolo), after losing his first two. Notably, this was the only one of these tournaments where the world was at stake.
- Soul Chess: Lelouch had to defeat Aizen three times before it was safe to say that he was not going to be leaving the ninth circle of hell any time soon. Even then, the first two times he had to rely on other methods to get rid of him: the first time by Geassing him to commit suicide, and the second by using Rita's power over the reincarnation cycle to briefly bring back Yamamoto and have him finish Aizen off for him. It was only the third time, after absorbing the Hogyoku, that Lelouch was able to defeat Aizen in one-on-one combat.
- The Connors encounter the T-1000 three times over the course of Terminator 2: Judgment Day (shopping mall, hospital, foundry) but only defeat him the third time.
- Within the foundry, the T-800 fights the T-1000 three times. The first time, the T-1000 crushes his arm in some gears. The second time, the T-1000 impales him with a metal pole, briefly "killing" him. The third time, the T-800 shoots the T-1000 with a grenade launcher and causes him to fall into a vat of molten steel, destroying him.
- Combining Star Wars Episode V: The Empire Strikes Back and Star Wars Episode VI: Return of the Jedi, Luke Skywalker directly encounters Darth Vader three times: the first time in Cloud City, the second time on Endor (where Luke fails to redeem Vader and is instead taken to the Emperor), and the third in the Emperor's throne room. The two never get close enough in A New Hope for it to count.
- In the Star Wars prequels it goes the other way around: Darth Sidious goes through three apprentices before he's able to defeat the Jedi: Darth Maul, Darth Tyranus and Darth Vader.
- Subverted in the Fritz Lang film Destiny: a young bride is given three chances to save her husband from Death. She fails the first and second times, and the third time as well, even though she's better equipped and gets a headstart. Notable in that it specifically invokes this trope as an allusion to European fairy tales.
- In Pact, this is an actual rule of magic, which holds power because of the numerous times that it has repeated-the belief of practitioners that it will work allows it to work. A third victory out of a set of three battles will reverse any losses taken in the previous two, and if you can defeat someone three times in a particular field the victory is guaranteed to be both meaningful and lasting. This leads to practitioner duels usually taking the form of attempts to either conserve strength for the third fight or prevent the third fight from happening, with the first two battles being irrelevant except as preparation for the third.
- It is common for bosses in video games to take three hits to kill. (e.g. Big Boo from Super Mario World, many The Legend of Zelda bosses etc.)
- One of the G.U.I.L.T. strains is fought like this in Trauma Center.
- Kratos in Tales of Symphonia is fought three times. The first two times, winning is optional, but Lloyd suspects he was holding back in those fights. The third is a Duel Boss, which Lloyd must win.
- You also fight Yggdrasil three times. First it's a Hopeless Boss Fight, second time it's a fight that you have to survive but can't win, and finally it's a regular fight you have to win.
- Similar to the Star Wars film example, the player has three encounters with Darth Sion in Knights of the Old Republic II. The first time, Kreia holds him off and loses a hand. The second time, the player fights him for a while in the Sith Academy before managing to escape. The third time, just before the final battle, the player must break his will in order to be able to kill him.
- Kyosuke's battles against Axel in Super Robot Wars Original Generation 2 might or might not be this. First round Axel is clearly winning before he's ordered to retreat, the next round might not really count since although both are eventually present Axel spends most of the battle dueling Lamia, and then Sanger, Kyosuke only showing up with the reinforcements that drive him off. Their third encounter (and 2nd duel) has Axel soundly defeating him and only stopped from delivering the killing blow by Kyosuke's allies. In their 4th encounter and 3rd duel Kyosuke successfully backs Axel into a corner with his upgraded mech (and essentially winning) but Axel is bailed out by an ally. Finally their 5th and final encounter and 4th duel has Kyosuke defeating him, destroying his mech and taking him out of the war.
- Dante has this with his twin brother Vergil in Devil May Cry 3. Dante loses the first fight. The Big Bad reveal interrupts the second fight. After they take care of the Big Bad, they have one more fight to the finish, with Dante defeating Vergil.
- Ike battles the Black Knight three times throughout Fire Emblem: Path of Radiance. The first time, after the Black Knight mortally wounds his father, Ike attacks him in a rage and is nearly killed himself. Much later, he encounters the knight a second time and challenges him again. He is again defeated, but impressed by his sudden increase in skill, the Black Knight reveals his armor's weakness so that the next time they meet they can have a fair duel. The third duel can be won, lost, or left unfinished, and is essentially a Luck-Based Mission. The sequel, Radiant Dawn, goes with Ike having won, but only because the Black Knight let him.
- Bowser is fought/encountered exactly three times in many Super Mario Bros. games, with him being fought as a level boss in the Dark World, Fire Sea and Sky in Super Mario 64, and in three different reactors in both Super Mario Galaxy and Super Mario Galaxy 2, with the last fight being the final boss battle. This also applies to the Mario & Luigi series (he's fought in the intro, part way through the game and in a posessed form as part of the final boss battle) and likely quite a few others too.
- Pointed out in Bob and George in the comments when it was invoked in one of the early confrontations over its entire run.
- Po vs. Lord Shen in Kung Fu Panda 2 is an interesting case. It's actually implied that Po could've easily won the first two times, but between his Heroic B.S.O.D. and Shen's Combat Pragmatism, he only emerges victorious in the third encounter.
- Weaponized by Candace Flynn in the Phineas and Ferb episode "Mission Marvel", where she determines that messing around with technology she's unfamiliar with has to work on the third try because her first 2 tries failed; she's right.
- Taiten Kusunoki had to attend three separate auditions to join The Prince of Tennis voice cast, and each time he tried pretty different characters. First he apped to play Kippei Tachibana but lost to Yoshihisa Kawahara, later lost the role of Taro Sakaki to Jurota Kosugi, and finally got in as Genichirou Sanada.
- King Henry VIII of England did not sire his coveted son, for whose birth he completely changed the social and religious landscape of England, until he met his third wife, Jane Seymour.