Angel aka Sorano Aguiera is a walking basket case with how much emphasis is put on her wanting to see her sister again. Her sob story in front of a justifiably furious Hibiki deserves a mention.
If you care about Jellal, the scene where he's apologizing profusely for Erza for what he did winds up with both characters crying by the end of it and Erza telling him that, now that she's done punching him in the face, if he buys her cake they'll call it even.
Everything to do with the relationship between Erza Knightwalker and Edolas Lelouch given the latter's brain damage and paraplegia. Poor Knightwalker.
Marianne's Death and everything leading up to it and after it until Lelouch’s departure can be seen as one of these or a massive collaboration of many.
Watching Erza go full on Berserker Tears as Morianna Feathermane reveals that she killed Erza's parents. Even in canon, Erza has never been this far gone or this enraged and in some respects, it's extremely heartbreaking.
Sindel is designed to be such a sympathetic villain that seeing her cry because it turns out that she misses Mavis, a person she saw as an older sister, might bring a tear to your eye. Hell, the resolution that she is forced into her 13-year-old self as a means of protecting everyone from her power really makes her a tragic individual.
It gets worse during Tenrou Island when Sindel gets to meet Mavis' spirit. Even the author admits to crying while writing the scene.
In chapter 100, both the scenes where Meredy and Ultear cry their eyes out when they begin their Heel–Face Turn will likely have you crying right along with them.
Undine's backstory tugs at the heart strings a little with the abrupt way her fiance is killed.
Kagura finding out that Zangetsu and Jellal are the same person. You can feel Kagura's pain escaping from the webpage and jumping out at you.
No. This one deserves a full explanation. Ahem. Jellal takes the disguise Zangetsu and meets Kagura in this disguise during the Grand Magic Games during the year X788, which is while Fairy Tail is still missing after their run in with Acnologia on Tenrou Island. Kagura has no idea that Zangetsu and Jellal are the same person, even saying to his face that she wants to kill him and not realizing she's talking to the person she wants to kill. She grows fond of him and outright falls for him over the course of a few days because he meets all her criteria towards a perfect boyfriend. And then it turns out that the very person she fell in love with is the very person she wants to kill and he is perfectly okay with that. Jellal was willing to die for Kagura both because he grew to care about her and because he wants to make up for what he did to her brother Simon. Ultear even gets in on the scene, trying to deflect blame to her given her role in the situation, but ultimately Kagura becomes resolved to kill Jellal, except she's unable to go through with it and breaks down crying because the person she met isn't the person she wanted to kill. Face it, if this was animated and put to proper music, we'd all be crying like little bitches. It's especially heartwrenching considering the build up to this scene.
This same scene is then followed up with Nivea's death, which while some might find was a dumb decision on part of draconichero, for those that were particularly attached to the character, it gets you right in the feels. There is a reason draconichero said he may as well have named the chapter I'm in an Ocean of Feels and I'm Drowning
While she wasn't around for long, many fans find that the death of Yuuki, the spirit from the immaterial plane that makes Gray a god slayer to be this.
Makarov finding out that Bob is dead. He breaks the news to Blue Pegasus and while he refuses to cry because that's what Bob would want him to do, he doesn't succeed.
Gets a bit worse nine chapters later in 207 where he receives his long missing wife's dead body just a few months after the death of Bob. The guy CANNOT GET A FUCKING BREAK!
Alysha devolving into Tender Tears during chapter 213 due to Archer and Alice showing her that there are other humans besides Travis that are good people at heart. And also because she never truly recovered from Travis' death.
Yukino watching her sister refusing to surrender by withstanding Libra's magic, even after Sorano breaks her ankle by standing up. Yukino breaking down and saying she doesn't care who is right or wrong anymore is heart wrenching.
Kasumi continuing to fight for VV out of fear for Kalina's life, especially when she defeats Undine, is incredibly sad. Fighting Your Friend in the worst way possible. And after Natsu interrupts her fight with Nessa, she breaks down in tears when Nessa tells her they're Not So Different when it comes to protecting their children.
Chapter 236 comes right off one of the douchiest cliffhangers provided by chapter 235 it looking like Erza has been killed. Most would say Pfft, Like You Would Really Do It, but this is Draconichero we're dealing with who goes out of his way to Gut Punch the reader and saying "Yes, yes I would". For a moment, you could almost be convinced that he actually did kill Erza off in a really tragic way, but then again Erza/Lelouch is the fucking flagship of Fairy Without Wings. So, Erza getting revived isn't all that surprising in hindsight, but oh god the FEELS.
Chapter 248 is this till the end. Fighting Spirit's hopeless fight against Tartaros is heart wrenching, since all members fall, one by one. If it wasn't because of Morrigan's intervention, characters we had known for years would have died just like that.
Chapter 255: Babasama's death, and how despite Sherry's and Chelia's efforts, they can't prevent their beloved guild master from dying from her wounds.
Chapter 257: The powerlessness of Fairy Tail being unable to defeat Roxanne without Natsu, Erza or Gildarts is almost palpable and they know it all too soon. But the most heartbreaking part comes at the end, when Roxanne claims she will kill Natsu and take his power, and despite Lucy's best efforts to stand up to her and defy her statement, she's incapable of refuting it. She's that strong, and when it downs to Lucy, she can only break down crying in despair.
And what's worse is Roxanne genuinely doesn't hold any malice towards Fairy Tail, but is so consumed by her desire for power and bonded to Tartaros, she can't stop until either she or Natsu are dead.