Woobie / Fairy Tail

• Natsu was abandoned by his parents, then his foster dragon disappeared without a word. Then his second father figure Gildarts leaves and best friend/possible girlfriend Lisanna dies. His only goal in life is to find Igneel, his foster dragon dad, and Igneel is violently killed by Acnologia before Natsu's very eyes.
• Speaking of Lisanna, Mirajane and Elfman lost their parents at a young age, then when all they had left was the three of them, Lisanna dies (and it's kind of their fault) then Lisanna has to deal with losing, literally, her entire universe and starting from scratch in a new one... twice.
• From what we see of Juvia's life pre-series it sucked. She was shunned and mocked as a child for unconsciously causing it to rain and any relationships she tried to form were undermined by her abilities. It's no wonder she was happy to join up with Phantom Lord when they were willing to accept her. With this backstory her tendency to go overboard when it comes to her feelings for Gray, comes off as her trying to hold on the person who freed her from the rain that overshadowed her entire life.
• Lucy. Oh, poor Lucy. She spends practically the entire series just trying to keep up with her friends in Fairy Tail, to little or no avail. She only joined Fairy Tail in the first place because her life up to that point had been stifling nobility. Her father started out caring and loving, but after her mother died when she was young, he began to treat her like an object rather than a daughter. Later it seems like their relationship is on the mend, and Jude actively takes an interest in Lucy's life in Fairy Tail. It even inspires him to rejoin the guild he used to be in with her mother before Lucy was born ...and then he dies while she's at Tenrou Island. One of her friends is attacked on the way to the Grand Magic Games, her friends' daughter gets held hostage, is brutally beaten up not once but twice. It seems like she might finally unlock her true potential as a celestial wizard, gearing up for a major spell that will take down her enemy...then it gets yanked out from under her, much to her humiliation. She gets captured for a plan she just found out that she was a part of, and Rogue's future self tries to kill her for what turns out to be his own selfish gain, instead lethally injuring her future self so that the dies in the present Lucy's arms. In the Tartaros arc, she is hunted down by much of the Dark Guild after Mard Geer petrifies everyone else, ultimately forced to snap the key to Aquarius, her first Celestial Spirit, to summon the Celestial Spirit King.
• Millianna has been getting this since she is having trouble keeping up with Kagura to be a worthwhile ally and being a victim of Minerva's sadism. Especially when the latter started clawing into her to pass the time.
• Another contender is Rogue. Not only does he have to often witness and deal with the horrific nature of his guild master, but he was forced to Mercy Kill his dragon parent. To add more, something in the future causes him to turn evil (while killing Sting in the process), and the present version is horrified at the fact he will be the one to bring the hell that they are currently suffering through. To add more fuel to the fire, Ultear thought to kill the guy in order to save everyone else and even when she doesn't, the fact that he could still become his evil future self, really hits hard.. You just want to hug the guy.
• Erza as well. She lost her parents to Zeref's disciples, and is caught, enslaved, and tortured while being forced to build The Tower of Heaven. Her attempt to set her Childhood Friend Jellal free fell through, and Jellal takes the fall for it. During the slave revolt, her grandfather figure Rob dies protecting her. She finally rescues Jellal, only to find that he'd lost his mind while being tortured. Jellal banished Erza from the Tower of Heaven, making sure she realized that she'd never be able to save the other children, and they were doomed to stay. 8 years later, Erza was kidnapped by these people, and was to be a sacrifice to Zeref. She fought her close childhood friend, Jellal, only to see Simon die protecting her from Jellal. She was nearly killed by the Etherion, which she offered herself to in order to destroy the Tower of Heaven. Fast-forward to the Oracion Seis arc, where Jellal had been turned good and was ready to live with Erza, Erza had to send Jellal to prison for all that he'd done, leaving her a sobbing wreck. She is frozen in time along with many Fairy Tail members during the Tenrou Island incident. Fast-forward to the Tartaros arc, she is kidnapped with Mirajane, and tortured by Kyouka, who used a magic to heighten Erza's sensitivity to pain, and is also threatened with the death of Mirajane.
• Wendy loses her Dragon foster parent (and she's introduced as far more emotionally fragile than the other Dragon Slayers), then befriends Mystogan only for him to suddenly abandon her to a guild, which she learns years later was all just an illusion created by a ghost, having to watch everyone she'd been acquainted to suddenly fade from existence, and this was shortly after watching her supposed childhood child get arrested for either a life sentence or execution before he could regain his (nonexistent) memory of her. Shortly after joining Fairy Tail, it also disappears as it's sucked into an Anima, and she and Natsu are captured and painfully drained of their magic after being told that their long-time Exceed partners betrayed them. She gets frozen in time for seven years, and much later gets mauled by a demon who tries to eat Carla in front of her, nearly dies self-destructing Face, and finally reunited with her long-lost foster mother only for her to pass on presumably less than ten minutes later.
• Gray beats them all in sheer amount. To start with his parents are killed by Deliora and he's taken in by Ur and raised alongside Lyon. Then he tries to beat Deliora and instead Ur performs a Heroic Sacrifice to stop Deliora, which results in Lyon hating him. Then he finds out years later Lyon wants to bring Deliora back and is forced to fight a guy who is essentially his brother. He ends up later confronting his technical sister who tries to kill him, gets stuck in magic stasis for seven years and gets mocked and for his performance in the Grand Magic Game's first day. Then he dies in the fight with the Dragons and is only saved by Ultear's Reset Button and goes on to fight a Demon who makes him freak out cause it reminds him of Deliora. THEN, in the Tartarus arc, he's told by Silver that Ur's sacrifice was in vain because Silver is Deliora possessing his dad's body and that Silver wants to kill everyone associated with Ur. The fact that this turns out to be a lie actually makes this worse; he's actually a Death Seeker zombie reanimated by yet another demon, and saving the magic world requires killing him along with the Necromancer controlling him. No wonder Gray is usually quite sullen. Makes you wonder what the hell else is next.
• Silver turns out to be this, as well as being quite possibly the best case of Woobie, Destroyer of Worlds since Zeref himself. Why does he seem like Tartarus' Token Good Teammate? Why was he visiting that grave? How did he know who Natsu was? He's not a demon, but he's not technically human, either; he was actually a corpse reanimated by Keyes, and was the closest Keyes had ever come to being able to fully resurrect the dead exactly as they were before. Silver began trying to destroy Tartarus from the inside, until he saw the Grand Magic Games, and discovered that Gray was alive, causing a major Heroic BSoD in which Silver decided he had no right to try to seek revenge for someone who was not only alive, but was definitely on opposing sides. Silver then began working as a true member of the Nine Demon Gates, and admits that he helped kill former Council members, simply because he wanted Gray to put him out of his misery. The ending of his fight has him begging Gray to kill him, with him wanting to join his wife, Mika, in the afterlife. The guy's been through every bit as much as Gray, if not more.
• If you separate out Jellal's status as Creator's Pet and try objectively to look at what he's suffered in his life, the list goes like this: starts out as a child in the "Tower Of Heaven", so as child slave labor, tries to free the people he loves and gets Mind Raped mercilessly as a result; is partially turned mad and continuously Mind Raped for years while he manipulates, tortures and enslaves the people he loves. Fast-forward to the Tower of Heaven arc, and he kills Simon mercilessly, tortures and tries to sacrifice the love of his life (all the while still being Mind Raped by Ultear by the way). Fast forward to the Nirvana arc and he wakes up as himself without his memories only to find out he enslaved, tortured and killed the people he loved (and this does haunt him and torture him psychologically for years once he gets his memories back), and at the end when he finally thinks he can live with Erza he is taken to prison. Fast-forward through the time-skip and he's spent six years trying to atone for his sins (having gone through the agony of regaining memories about him acting evil and being Mind Raped, which must have been great), finally find out Erza's alive and won't be with her because he doesn't want to hurt her and taint her with his problems and issues (by the way, actually hurting Erza by doing this, which adds to her Woobie status), and is still being hunted by the Magic Council. Fun. He may not qualify as a Woobie character-wise, but his past and all the psychological agony he's suffered certainly should get a mention at the very least. Oh, and making an ass out of himself in front of Erza in the Grand Magic Games in his match against Jura would have been fun too...although mostly that was just hilarious.
• MAVIS. As if her Dark and Troubled Past wasn't bad enough, where she was treated like absolute dirt by the guild master of Red Lizard, she watched her only friend die, and then spent her entire childhood up until her early teens completely isolated with only what amounts to an Imaginary Friend for company. It isn't long before she meets Zeref, who taught her a spell that would later be used to save her friend's life, at great personal cost: losing the ability to age, which later turns out to be a symptom of Ankhseram's Curse, something she absolutely refuses to believe and results in her crying Tears of Fear. When she inevitably kills somebody because of this, she suffers a full-blown Despair Event Horizon, and runs off to live alone in the woods, every bit as much of a weeping, self-loathing, death-seeking emotional wreck as Zeref himself. When they two finally reunite, Zeref starts going into his own mental breakdown, and Mavis promises that they two of them can find a way to break the curse together. Zeref confesses his love for her, and kisses Mavis. And then she dies. A century later, the same man whom she came to love starts losing it all over again, becoming an Omnicidal Maniac while she can do nothing but helplessly watch. Of all characters to go through a Trauma Conga Line, she ranks among those who deserve it the least.
• Yukino. She grew up with Abusive Parents, and while her Cool Big Sis stood up for her, she got kidnapped by Zeref cultists. She eventually made it into Saber Tooth, but was painfully aware that she was only a reserve member for the Grand Magic Games, which likely drove her to bet her life against Kagura. After losing and being spared, she's kicked out of the guild in the most humiliating manner possible, and the "Twin Dragons of Saber Tooth" manga implies that she was traumatized by the experience. She eventually does find her sister again, only to find out that Sorano(aka Angel) feels as though she's done too much evil to reunite with Yukino or consider herself her sister until she atones.