Third Time's the Charm

A Sub-Trope of the Rule of Three, this trope extends to confrontations in a particular work. When invoking this trope, a protagonist will, over the course of the story, confront a particular villain or antagonist roughly three times in succession. The first two times the protagonist makes an attempt at defeating him however, he will lose, or at the very least have severe implications that had the battle gone on longer, he would have lost.

Sometimes this particular trope can provide good motive for Character Development but at the same time may fall into the trap of the antagonist leaving him alive for little adequately explained reason if the method of the hero's survival from the defeat isn't portrayed the right way. Often, these first two losses will be quick and supremely one sided, though this may not always be the case, particularly with those certain characters where such losses are always due to cheating or some other unfair circumstances.

However, then comes the third confrontation, which sometimes takes place after a few or even several little boosts to make the match more even, and now the gloves are off. This time, for sure, the hero will finally be able to defeat his foe, no matter how much damage he takes in the process. And then by the end of their third confrontation, this time for sure, the hero will stand triumphant.

This trope is often invoked in order to stress to the audience just how difficult it is to overcome this particular obstacle without dragging it on to the point of madness. The magic sweet spot for this formula, as is almost natural, appears to be over the course of three confrontations. Sometimes this trope can also be invoked in the same battle, if the hero all but loses yet still manages to get up on sheer willpower twice over the course of the fight, though generally it almost always happens over the course of three separate battles.

Mainly occurs when the Rule of Three is invoked in the protagonist's confrontations with an antagonist.

Anime/Manga

 * 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
 * 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
 * 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.
 * Shin Asuka's initial confrontations against Kira in 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 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.
 * 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, he escapes with . In the third, Muhyo.
 * Between Magical Girl Lyrical Nanoha As and Striker S, 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, bu Arika is victorious in the third.

Literature

 * Arguably the titular Harry Potter had three direct confrontations with Voldemort over the course of the series in which a battle of sorts actually took place between them, though granted most of time he was pretty much just running for his life, or watching as someone else confronted him.

Film

 * The Connors encounter the T-1000 three times over the course of Terminator 2 (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.
 * In Star Wars, 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,  Notable in that it specifically invokes this trope as an allusion to European fairy tales.

Video Games

 * It is common for bosses in video games to take three hits to kill. (e.g. Big Boo from SMW, many Legend of Zelda bosses etc.)
 * One of the G.U.I.L.T. strains is fought like this in Trauma Center.
 * 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.
 * 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 OGS 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.

Web Comics

 * Pointed out in Bob and George in the comments when it was invoked in one of the early confrontations over its entire run.