[[caption-width-right:320:Iím not really sure why it is Ė I feel like tears are going to fall. But if I cry or make a sad face, Iím sure the tropers would be troubled.]]

* "Sakura and the Calendar of Memory", wherein [[spoiler: Nadeshiko's grandfather Masaki reconciles with Fujitaka, after Sakura learns of their relationship and gets him a birthday present]].
* Also, "Sakura and Her Memories of Her Mother". [[spoiler: Especially when Sakura cries happy tears after seeing that the cause of the troubles was ''not'' her mother's spirit.]]
* And the Final Judgement, [[spoiler: before Kaho's [[ResetButton Bell of the Moon]] eliminates Sakura's loss to Yue, and she and everyone she knows forgets whomever they loved the most]].
** Adding to that, [[spoiler: Sakura is in the spot where Yukito's house is and crying, and she starts to hear the voices of her friends call out her name for a few seconds. Then the Song Card fades in and starts singing Tomoyo's song. Soon, silhouettes of Tomoyo, Li, her classmates, Kero, Touya, and Yukito appear behind her, and sing along. Doubles as a Crowning Moment of Heartwarming.]]
* [[spoiler: Sakura crying in Syaoran's arms after she pulls her own IWantMyBelovedToBeHappy on Yukito and encourages him to hook up with his beloved Touya. She's almost completely [[StepfordSmiler happy and cheery]] when speaking to Yukito himself, but once she's with Syaoran in the park, she explains what she just did, and then she starts crying and saying that even if she did the right thing, and she doesn't regret it, it still ''hurts''...]]
** [[spoiler: Keep in mind Sakura's crush on Yukito was a large part of her character established from the start of the very first episode. So many stories were devoted to her trying to get his attention and yearning to be with him forever. Sure, we know she has Syaoran by this point, but it's still rather crushing to see her get told by the love of her life that it was never meant to be.]]
** And Syaoran in the same scene in the manga. [[spoiler: The ''look'' on his face when Sakura said that she told Yukito she loved him. He knew she liked Yukito, but that really had to hurt!]] And then in the next chapter, [[spoiler: he decides that he won't tell Sakura how he feels, because he doesn't want to upset her.]] Dang!
* Another mix of TearJerker and IWantMyBelovedToBeHappy in the series is [[spoiler: Meiling's return to Japan, where she breaks off her engagement to Syaoran and tells him to go for Sakura, but then she bawls her heart out on Tomoyo's lap because she loves both Sakura and Syaoran too much to hate them for her heartbreak.]]
** Given [[spoiler: Meiling's]] {{Scrappy}} status at the start (although she later graduated to JerkWithAHeartOfGold), it was quite a shock when hearing her heartbroken sobs. Couldn't help but cry in concert with poor [[spoiler: Meiling]] after that.
** And props to the voice acting, because many times when this is done, the crying comes off as hysterical and gut-wrenching, sure, but with [[spoiler: Meiling]] it was the kind of ugly sobbing that sounds like it's torn out of [[spoiler: her]] very being.
** Adding do this, [[spoiler: Meiling's]] face when [[spoiler: she first realises Syaoran and Sakura are on a FirstNameBasis as he calls her by name. It's even more heartbreaking because you can tell how focused she is on Syaoran, as she never noticed Sakura twice calling him by name; it wasn't until he said her name that she noticed it]].
** [[spoiler: The build up to this makes the entire episode painful to sit through. Syaoran is blatantly guilt ridden at having to break the news to Meiling and is only more pressured when she arrives to Tomeda to hasten it. Even Tomoyo, who was gleeful at the thought of shipping him with Sakura, notices the moment Meiling has put it all together and feels bad. Knowing she will get her heart broken, she cryptically offers herself as a shoulder to cry on when the news is broken.]]
-->'''Wei:''' [[spoiler: Meiling-sama truly is a kind person...]]
-->'''Syaoran:''' [[spoiler:''*sadly*'' Yeah...]]
* Sakura witnessing Clow's death is a double TearJerker: [[spoiler: not only do you get Clow saying goodbye to his creations, you get to see Sakura's face when she hears Kero and Yue claim no one will ever be as good as him.]] ''Ouch''.
** The manga steps up on Yue's part, where he cries out that he'd rather sleep in the book forever, and he doesn't want to wake up anymore.
** Later in her conversation with Clow, Sakura breaks down, stating she is unworthy of being master and could never match him. Clow just smiles and assures her she'll do fine as Sakura, and is glad she took the role. How many in real life have desired such reassurance and closure from those long gone?
* The following episode, where [[spoiler: Yukito (now aware of Yue's existence and his status) angsts because [[TomatoInTheMirror his whole life as a human is a lie]], but Touya reassures him that their common memories are true]], and this happens right before [[spoiler: Sakura's aforementioned IWantMyBelovedToBeHappy moment towards Yukito and Touya, followed by her breakdown in Syaoran's arms]] brought even more tears.
* Sweet lord... the end of the episode with The Mirror. That particular card starts as a trickster with shades of JerkAss, but when [[spoiler: Touya shows her genuine affection]] ''and'' [[spoiler: she's so guilty after her HeelFaceTurn that she drops Sakura hints about her identity so she can seal her as atonement]], she becomes TheWoobie. Poor, poor Mirror card. *sob*
* For a one-episode character, Youko was a massive {{woobie}}. Almost any girl who likes her classmate in secret and is too shy to tell him/her can identify with her struggles, specially when [[spoiler: Touya politely turns her down... and like Sakura would do later, she takes it as well as possible, but still can't help crying.]]
* From the first [[TheMovie movie]], Madoushi's [[spoiler: finally accepting the fact that Clow Reed is dead...and realizing that no, she will ''never'' get to confess her love to him.]] Her dialogue makes it worse.
-->'''Madoushi:''' [[spoiler:Is Clow Reed really dead?]]\\
'''Sakura:''' [''wordlessly nods'']\\
'''Madoushi:''' [[spoiler: ...But...I waited...[''sadly begins to dissolve into water''] ]]
* The scene where [[spoiler: Touya willingly sacrifices his powers and transfers them to Yue, both to have Yue protecting Sakura ''and'' to keep his beloved Yukito by his side.]] Made even "better" when [[spoiler: Yue warns him that he won't see Nadeshiko's spirit again, and Touya says it's okay because being able to see her but not tell anyone else that she's there caused him pain.]] The kicker? [[spoiler: When the power transfer is done and Touya passes out in the fully recovered Yue's arms, he hears some noise and uses a gust of wind to open the door. ''It's Sakura, who has heard everything, and [[TenderTears is sobbing]] [[HeroicBSOD her heart out]] because she blames herself for [[HeroicSelfDeprecation not being powerful enough to sustain Yue]]''. And then she tearfully vows to protect Touya forever, like he has done to her]] Waaaaah!
** Sakura is heartwrenching here. She isn't just crying because she was on the verge of losing Yukito and Yue because of her lack of power, but also because of how badly she misjudged Touya. Whenever Kero brought up the possibility that Touya was on to them, Sakura dismissed it out of hand, saying that if her brother knew what she was doing, he'd tease her mercilessly. Come to find out that he ''did'' know all along, kept her secret, ''and'' gave her space to let her take care of matters herself.
* In Episode 69, Kero and Yue are ready to pull a HeroicSacrifice, placing themselves in Sakura's wand, which could risk trapping them inside forever. Sakura, upon realising this, pleads desperately against it, bursting into tears and hugging Kero as hard as possible. Kero can only nussle her gently while Yue gently convinces her to agree to it.
** In the the anime, she hugs Kero, and Yue comes over and lays a hand on her shoulder. In the manga, Yue knelt to speak with her, so she was able to hug them both at once, making it clear that Sakura doesn't just care about Kero and Yukito, but she loves Yue, too.
** Syaoran also lends his energy to her, and like with Kero and Yue, she doesn't want to lose him either but he insists on helping her. In the manga, he collapses while contributing his own magic with a look of shock knowing that if she is unsuccessful, she will lose Syaoran too.
* The second movie has the Nothing Card systematically erasing everyone Sakura cares about from existence.
** The Nothing as a WoobieDestroyerOfWorlds. Imprisoned beneath Clow Reed's house in darkness, unable to escape, and [[LonelyAtTheTop separated from her friends]] and created with solely negative magic to act as a balance to the positive magic of the other Clow Cards. We learn just how much of a BrokenBird she is when she steals all of the cards, only for them to turn against her, causing her to break down in tears until Sakura offers a spot amongst her friends as a Sakura Card.
* Sakura's DisneyDeath in the elevator in Episode 57. Just the close up shot of Syaoran's very still face as he repeats the image of her falling to her supposed death over and over in his head. His face contorts in heartbreak, like he's about to break down completely. Instead we get this for the very first time:
-->'''Syaoran:''' SAKURAAAAAAAAA!!!
* Any scene where [[CryCute Sakura cries]] is just heartbreaking to the point where you just want to hug her every time something heartbreaking happens. (And thus was [[{{Moe}} a concept born]], really.)
* In an effort to remove most of the romance from the series, Nelvana ended up ''adding'' an unintentional tearjerker near the end, with Sakura and Syaoran never reuniting at the end, unlike in the original.