Groundhog Peggy Sue

So we have your Peggy Sue Fic in which a character is suddenly sent back to the beginning of his story with future knowledge and/or powers to Set Right What Once Went Wrong.

Then we have your Groundhog Day Loop Scenario in which a character is stuck in a repeating time loop, forced to re-live the same moments over and over again until a certain condition is met.

When you combine these two you get the Groundhog Peggy Sue, in which a character is forced to re-live a significant portion of his life over and over again, always looping back to a certain point to his childhood if he dies or reaches a predetermined point in time. The protagonist tends to be a Failure Knight if the loop depends on him saving someone or killing the Big Bad. Sometimes the person looping is trying to avoid some kind of disaster; however, no matter what he does, the future never changes unless of course it gets worse.

In some versions of this trope the characters live through each repeat of the loop fully, while in others they make a change in the past and are instantly transported to the "present" to see what their actions had changed.

Subtrope of Groundhog Day Loop.

Anime and Manga

 * Causing this is basically the result of wish in Puella Magi Madoka Magica..
 * This occurs in the manga Shin Mazinger Zero, with Minerva X the only one aware of it.

Comic Books

 * At the end of Whatever Happened to the Caped Crusader?, Batman is reincarnated as an alternate universe version of himself; it's stated that, in lieu of a traditional afterlife, Batman is destined to spend eternity being Batman, living out different versions of his life over and over again.

Fan Fiction

 * Harry Potter and the Wastelands of Time: Harry is stuck looping to the same summer before his sixth year whenever he dies. Having lived over a thousand lives this way he still can't seem to outpace Voldemort.
 * A similar oneshot, Sisyphus, involves Harry stuck looping to the moment where he learned he was a wizard whenever he dies. He eventually
 * All is Relative Except the Stubbornness of a Demon: Because the Kyuubi refuses to die, Naruto is always sent back in time to the day before the Genin exam whenever he dies whether it is in battle or of old age.
 * In Myriad Ways: Naruto dies at the Valley of the End and strikes a deal with Death to Save Sasuke and starts looping back to before the Chuunin exam.
 * Rewind: Charmcaster uses Time Travel magic to trick the Tennysons, rewinding whenever she gets caught. It. Gets. Worse.
 * The one-shot The Chosen from the Avatar: The Last Airbender collection The Ember Island Lighthouse. Ozai goes through his life with different allies each time.
 * Chunin Exam Day: Due to an accident involving Kyuubi chakra and Orchimaru's barrier, Naruto relives the Chunin Exam over and over. He ends up getting a harem as well when he figures how to bring other people into the loops.
 * Right Moments: Due to meddling by Happosai, Ranma ½ is stuck repeating the day after the failed wedding from the end of the manga, a repetition which won't end until Ranma himself is satisfied that the day he lived was absolutely perfect.
 * Samsara: Shinji finds himself in a Groundhog Day Loop in which he keeps on living the same day over and over again, with nobody else aware of it. Though he fools around with it, he ends up upsetting Asuka when he becomes too reckless, prompting him to try to make her happy. He finally exits the loop when he succeeds.
 * Time Braid has Sakura going back to the beginning of the Chunnin Exam over and over again, with the timeline usually resetting with her death, failing the test, or not preventing the later attack from Orochimaru. Eventually, she finds out that Naruto, Sasuke and Hinata are also going through their own personal groundhog loops, each with various states of sanity.
 * Infinite Corridor looks like it's going to be this.

Film

 * The Butterfly Effect
 * This happens in Primer, but we don't know for how long.

Literature

 * Replay, by Ken Grimwood, revolves around the protagonist and a few others going through the titular Replays which take the replayer back to an earlier point in his/her life, to relive the time period until his/her death (the same date and time in every loop, although the exact date and time differ from person to person). Problem is that each replayer finds that his/her replays are beginning later and later...
 * , by Stephen King. At the end, when the protagonist finally attains his lifelong goal, it results in him being popped right back to where we first met him. This is implied to have already happened several times, because he still hasn't quite gotten it right yet...
 * The short story Spring Fever implies this. Having married a conservative businessman, the protagonist is bored with her comfortable-but-bland lifestyle, and daydreams about her first love, Ray. Her daydreaming seamlessly melts into the past, where she chooses to "go all the way" with him... Back in the present, she is now unhappily married to Ray, and the ending heavily hints she's about to repeat the loop again.
 * Played with in The Time Traveler's Wife. Henry constantly goes back in time to his mothers death, but cannot do anything.
 * Sorbet is about Hadley Mint trying to wake up from a nightmare...but it's a nightmare that loops unless she can figure out how to stop the loop. There have been talks of zombie/vampire/something activity before she went down for a nap, since this is the Gerosha universe. So she is unable to determine at what point the dream is or isn't based on a real scenario. She has to figure out what the one thing is that's different about how she wakes up, in order to find out what's real and what's just another dream loop cycle. Each time she has a dream loop cycle, things start almost exactly the same. It's her actions that disrupt the order. She isn't sure which is more frightening...the zombies, or finding out she is still dreaming.

Live-Action TV

 * That Was Then: A short-lived 2002 series in which the protagonist repeatedly goes back to his High School years in an attempt to make things better. Similar to The Butterfly Effect.
 * Happened to the SG1 in Stargate SG-1 when they were trapped in a Lotus Eater Machine that forced O'Neill to relive a failed Special Ops action, and Daniel to relive the death of his parents.
 * In the Supernatural episode "Mystery Spot", Sam was stuck in a Groundhog Day Loop which reset itself to the moment he woke up on Tuesday morning every time Dean died. Sam spends several hundred Tuesdays trying to prevent Dean's varied and bizarre deaths, convinced that if he can just keep Dean alive until Wednesday, then the loop will be broken.

Music

 * This trope was revealed to be the actual plot behind BTS's multimedia project "BTS Universe". The webcomic Save Me and the novel The Most Beautiful Moment In Life: The Notes 1 revealed that has gotten in a time loop where he tries to save his dear high school friends from tragic ends, but as the videoclips and the rest of the media on the project has shown, the problems of those kids are simply too much for a person to tackle them, and he isn't exempt from trauma either, so his efforts are always foiled due to his mistakes on understanding or handling the situation, restarting the loop again and again.

Video Games

 * This is basically what happens in video games in general, if viewed from a certain standpoint.
 * The plotline of BlazBlue: Calamity Trigger, from the perspective of Rachel Alucard.
 * The Reveal at the end of Calamity Trigger reveals there is a second one at work. Unlike Rachel, has been trying all long to make things even worse.
 * The When They Cry franchise—both Higurashi no Naku Koro ni (though we're not told who the Peggy Sue is until the end of the first season) and Umineko no Naku Koro ni (in an odd meta way).
 * You can turn your companions into this in Ephemeral Fantasia; until you bring them out of their Groundhog Day Loop, they're unaware of the repeating five-day cycle.
 * The plot of Shira Oka: Second Chances is that the protagonist must repeat high school over and over again until he can snap out of it. He may be forced to restart again if he dies or makes the wrong decision that ends up in an unhappy ending.
 * Majora's Mask features Link in a three day time loop trying to stop Skull Kid from dropping the Moon on Clock Town.
 * A particularly horrifying and tear jerking one is the fate of Jyoji Hijiri in Shin Megami Tensei Nocturne. He is essentially trapped within the endless cycle of death and rebirth that Kagutsuchi has imposed upon the worlds. He witnesses the end of one world, suffers within the Vortex World and dies, and then is reborn in the new world just in time to watch the end once more. Furthermore, he is cursed so that he can never influence these events, essentially making him a spectator for all eternity.
 * Embric of Wulfhammers Castle revolves around this trope... Or Does It?
 * In Alan Wake's American Nightmare, Alan's Evil Counterpart, Mr. Scratch, attempts to create a no-win situation for Alan by capturing him in a time-loop; even if he survives the deathly trials of the loop, he will still have to go through them again. However, as Alan and the three women stuck with him in the loop retains memories of the previous cycles, they eventually become Dangerously Genre Savvy and begin to coordinate their efforts to drive the loop Off the Rails.