When fans think about the Fairy Tail Guild, so many things come to mind: friendship, laughter, drunken fights, etc. Magnolia Town's rowdy bunch of wizards are iconic for their lively attitudes and heroic nature, easily making them an idyllic Shonen team. However, just because they are the anime equivalent of Harry Potter superheroes doesn't mean that they're perfect.
While it is easier to think about all of the guild's laughs and victories, they do have a long history of mistakes and defeats that equally feed their identity. No guild is perfect, and Fairy Tail in particular has had plenty of moments to learn and grow from. Some of these are iconic losses that make their rebounds even greater, and some are poor decisions that could sober even Cana Alberona.
10 Invasion From Phantom Lord
While fans have practically seen the iconic guild hall destroyed on a weekly basis, either by some world-ending threat or because Natsu got into another fight, that doesn't loosen the impact of the first time it happened on screen. Fairy Tail is just one of many guilds that seek to protect and compete for work in Fiore.
When Team Natsu returns from their previous battle, they are not welcomed by open arms but a tragic view of their guild hall destroyed by giant iron beams (surely a fond memory for Gajeel Redfox). With some of the strongest members gone, a competing guild, Phantom Lord, took the opportunity to try and level the competition. In terms of both aesthetics and strength, Fair Tail didn't look good in this one.
9 Losing Lisanna
Fairy Tail isn't exactly famous for its character deaths. Despite the fact that the guild once hosted dozens upon dozens of wizards going off on dangerous missions, the series never touches on if any of them lost their battles (if they even lose at all). This and so much more is what made losing Lisanna all the more impactful.
Lisanna was part of what was essentially the strongest family within Fairy Tail and was Natsu's go-to partner before Lucy. Her "death" in battle (thanks, Edolas Arc) was a surprising one for a guild famous for its constant victories, forcing her sister, the once brash Mirajane, to change her personality and go into temporary retirement.
8 Laxus
Dwelling within the guild's second floor was one of their stronger members whose demeanor was anything but nice. This would be Laxus Dreyar, an S-Class wizard and the grandson of Guild Master, Makarov Dreyar. His own father was a rogue wizard who taught him to value strength over everything, an ideology that Makarov didn't think could go wrong when he took him in.
Laxus is infamous for taking the invasion from Phantom Lord in an incredibly bad way, convincing himself that he personally needed to clean house and take Fairy Tail as his own. This involved threatening the entire community of Magnolia, turning a bunch of Fairy Tail members into stone, and personally fighting some of its strongest characters.
7 Defeat To Acnologia (Tenrou Island Arc)
Right after Fairy Tail defeated their second master (more on him later) which happened right after they already went through a strenuous, shonen-style exam arc, they were greeted by another even more challenging obstacle in the form of a big, bad dragon. Natsu would foolishly try to use his Dragon Slayer expertise, only to learn how feeble his skills really were.
With the entirety of the guild able to do nothing else, they join hands as they accept their fate. While the magic of deus ex machina would ensue later, this scene not only makes this defeat a sad one but one of the most definitive losses in Fairy Tail's history.
6 Everything In The Seven Year Time Skip
Thanks to Fairy Sphere, the guild members on Tenrou Island were able to survive Acnologia's onslaught but unfortunately could only revive seven years later. Their absence, in turn, would produce a lackluster time skip, not just because of the minimal shift in the status quo but the definitive proof that Fairy Tail is nothing without its good members.
After seven years, Fairy Tail has lost all credibility, most of its members, and a lot of work. Macao took on the mantle of guild master but is easily pushed around by the shiny, new guild, Twilight Ogre. To give a quantitative value to their failures, Fairy Tail would also sustain a seven-year losing streak at the Grand Magic Games. If nothing else, the phrase "too many eggs in one basket" comes to mind.
5 Picking Guild Masters
While the title of "Guild Master" still sounds important, it has a shaky history within Fairy Tail. Their second master, after learning about Eternal Magic, would turn to the dark arts and form a Dark Guild. The guild's fourth master was Macao who was just more or less a substitute teacher.
Whenever Makarov personally tried to pass on the title to a worthy successor, it would just bounce around between people until it would inevitably come back to him. At the moment, Fairy Tail does seem to be fine, but it's not exactly planning out its future or willing to let an old man retire.
4 The Moments Before Last Ages
The events prior to Ultear using Last Ages were some of the grimmest in Fairy Tail's history. As dragons rampage across Fiore and Future Rogue resides in the dark skies, several key players become incapacitated, such as Makarov becoming buried under some rubble and Gray just straight up dying.
It's a humbling moment for the guild that shows how much things can turn for the worst within just a minute. Ultear, however, would give the ultimate sacrifice as she would use up some of her own lifetime to use Last Ages to return that ever so precious minute.
3 Lumen Histoire
Lumen Histoire, aka Fairy Heart, is perhaps Fairy Tail's greatest secret and controversy. It is the preserved body of the guild's first master, Mavis Vermillion, and possesses both infinite magical power as well as Ankhseram's Curse. The guild's second master, Precht Gaebolg, tried his best to resurrect Mavis after retrieving the body from Zeref, but would only become tempted by the body's seeming well of power.
Gaebolg's successor, Makarov, would later disband Fairy Tail when the secret of Fairy Heart was revealed. In the effort to keep people from hunting down or fighting over Fairy Heart, it would be the sole reason for the guild's demise.
2 Abandoning August
On top of experimenting on Mavis' body and starting his own Dark Guild, Precht Gaebolg also abandoned Mavis' and Zeref's son, August. While the logistics behind August's birth are up in the air, Precht was put in charge of another life after one of his experiments. Not wanting to kill the child (at least personally), he did something only slightly better: put August in a basket and let him drift down a river.
August would have to survive the rest of his life through thievery, that is, until he meets his father Zeref. Afterward, August would learn from Zeref and become one of his most powerful cohorts, later facing Fairy Tail as one of their most dangerous, final enemies. Life had a funny way of turning around in this one.
1 Defeat To Acnologia (Tartaros Arc)
Acnologia really bolstered that final boss feel, not only by defeating Fairy Tail once but twice. After the guild put up with a lifetime of heartache during their battle against Tartaros, they would be rewarded with the friendly sight of everyone's favorite society-destroying dragon.
This would be followed by the revelation of the whereabouts of the Dragon Slayer's masters, as they would rage another, epic battle in the wake of Tartaros. As amazing as the sight was, the series just wasn't ready to beat its big bad just yet, and some sad anime moments follow. This would ultimately be the most humbling moment for Natsu Dragneel, and the inspiration for a real training/time skip arc for the guild.