[[caption-width-right:253:[[SandInMyEyes I just have dirt in my eyes.]]]]

* Episode 13, when [[spoiler: Angemon knowingly sacrifices himself to protect TK]] and the other chosen children.
--> [[spoiler: Original: Angemon: Sorry, Takeru[...]Surely we will meet again...if that is your wish...]]
* Episode 22, where Matt tells TK he's leaving for a few hours and never returns. TK was in 2nd grade. This could border on nightmare fuel.
** That TK and Tokomon split up in the first place, all thanks to [=DemiDevimon=]'s lies. And then the first sight we see of Tokomon in the episode is collapsed by TK's digivice and crest.
* Episode 26, Biyomon wants to protect her friends from their newest enemy, Myotismon, but Sora holds her back and tells her not to or she'll get hurt. Biyomon cries "Sora, why can't you understand me?" Cue Sora realizing that she's behaving like her own mother towards Biyomon, so that this whole time, her mother was always overprotective because she loved her and was looking after her. Biyomon/Birdramon then attacks Myotismon only to be impaled in the chest by Myotismon's attack. Sora cries "Birdramon, no! ''I love you!''" [[CrowningMomentOfAwesome And then her crest of love glows.]] Made poignant by the fact that Sora's been feeling this whole time like she's never known love and can't truly love anyone. This is also very much a CrowningMomentOfHeartwarming.
* In TheMovie, the part taken from the Digimon: Adventure short film, when Greymon battles Parrotmon. Who doesn't want to cry when [[spoiler: two kids are seeing their first Digimon have to duke it out and almost die]]? Of course, this soon turns into a CrowningMomentOfAwesome when [[spoiler: Tai wakes Greymon up the same way Kari awoke him (with her whistle), and he kicks that goddamn bird's ass.]]
** When little Kari is crying out for the sacrificed Digimon who just saved her and her brother's life, and Tai's voice connects us to the future story, followed by [[http://www.youtube.com/watch?v=8vAQlYpt6m4 this]]. [[ABoyAndHisX A boy and his digimon]].
** Her dialogue just as sad in the dub...As Tai wakes up in the middle of the rubble, Kari is already awake, shouting for Greymon to stay and play horsey with her.
* The end of episode 21: Hikari wordlessly begging her brother not to leave her and his sorrow as he realizes he has to leave her again are nothing short of heartbreaking... the music doesn't help.
** The arc that follows, where everyone is separated due to Tai's absence. Joe is stuck buried in debt at a digital world restaurant, Demidevimon drives a rift between TK and Tokomon, Izzy gets stuck in a dark void and is tempted by a Vademon to give up his desire for knowledge (which renders him submissive), Mimi is being waited on by a group of Geckomon and Otamamon and starts to go crazy with power, Matt is struggling to find TK and Sora is the only one who isn't lost, but thanks to Demidevimon she's convinced she'll never truly know love and that her crest will never glow, so she can't bring herself to face her friends (though that doesn't stop her from [[TeamMom helping them from the shadows]]).
* Pumpkinmon and Gotsumon's deaths. Although they were technically Myotismon's henchmen, they were only interested in [[HarmlessVillain causing mischief and having fun]]. They even befriend Matt and TK, and when Myotismon himself shows up, Pumpkinmon and Gotsumon pull a YouShallNotPass to allow their new friends to escape, despite not being anywhere ''near'' Myotismon's power level. The english dub claims that Myotismon [[NeverSayDie "banished them to his dungeon"]], but it's pretty clear he actually killed them.
* Gatomon's back story is one giant TearJerker. She is accidentally abandoned, waiting all her life for her "special person" only for her to never show up, and then picked up by Myotismon only to be abused and warped into a super-soldier? It's too much.
* [[spoiler:Wizardmon]] performing a DivingSave for Kari and Gatomon. The conversation that ensues just clinches it.
-->'''[[spoiler:Wizardmon]]:''' "Are you alright, Gatomon?"\\
'''Gatomon:''' "You saved me... I'm sorry."\\
'''[[spoiler:Wizardmon]]:''' "About what?"\\
'''Gatomon:''' "Sorry I got you involved in this..."\\
'''[[spoiler:Wizardmon]]:''' "Don't be sorry. I don't have any regrets. If I hadn't met you, my life would have had no meaning. [[SugarWiki/HeartwarmingMoments I'm glad that you and I were friends...]]\\
'''Gatomon:''' "... the best forever..."\\
'''[[spoiler:Wizardmon]]:''' "Thank you for everything, Gatomon..."
** Just as bad is Kari's BigNo in the Japanese version...
** That has got to be the saddest moment in all of the first season... because [[spoiler: he doesn't get better. Since he died on Earth, he was unable to turn into a Digi-Egg.]]
** What makes it sadder is the reason behind all of it: [[spoiler:Wizardmon sacrificed himself not for the [=DigiDestined=], not for the fate of the Digital World ''or'' the real world, but for Gatomon's happiness. He was loyal enough to her that [[IOweYouMyLife he would do anything for the sake of making her happy]], even if it meant taking a Grisly Wing for her. And he had no regrets for it as long as she was happy in the end, even though it meant they may never see each other again. [[ThePowerOfFriendship And this is why his death is one of the most powerful sacrifices in the series]].]]
*** Here's [[http://adventuretri.tumblr.com/post/105551896774/so-i-was-reading-the-digimon-adventure a section from the novelization]] that makes things ''twice'' as heartbreaking - he ''knew'' he would never return to the Digital World, but he went anyway, because of his UndyingLoyalty to Gatomon.
* Izzy's backstory. That's all. Even Tentomon was bawling when he learnt about it.
* The mass memorial that followed [[spoiler:Whamon's death--Wizardmon, Chuumon, Piximon, and now Whamon]]--was what did it for me. The fact that this was ''that early'' in the Dark Masters arc says so much.
* [[spoiler: Leomon's death and Ogremon's reaction to it]]
** FridgeHorror when you realize of all the dead digimon by this point that come back, Leomon isn't one of them thus starting the tradition of [[KilledOffForReal killing Leomon forever]]
*** Not really. Remember, time on the two worlds was synced up after the final battle so there was only a couple years between the end of series one and 02, that's not enough time for Leomon to be reborn and digivolve all the way back to Champion level. That's not even enough time to get to Rookie.
*** Thankfully, by the time Anime/DigimonAdventureTri starts, HesBack in his Champion stage... [[spoiler:only for him to [[KilledOffForReal die in the real world]], thus making him a true part of the cycle. It never ends... *sniff*]]
* Tai's story about how his little sister Kari [[spoiler: nearly died]] because of his irresponsible actions when he was just a kid. What really hurt were Kari's first words back from the hospital: [[spoiler: ("Tai.. I'm sorry I can't kick the ball very good. You'll probably never want to play with me again").]]
** Surprisingly, the scene was especially tearjerking in the dub due to [[HeReallyCanAct Joshua Seth's performance]]. No offense to Toshiko Fujita, but Seth blew her rendition out of the water - you can really ''buy'' the fact that that the poor kid was breaking down in tears, struggling just to talk through the sobbing. This is easily one of the dub version's most emotively powerful parts.
*** The whole scene is tearjerking in itself, but the whole thing is made worse is the fact that ''his mother outright HITS him'' and yells at him like he committed bloody murder (the shot of Tai's mom hitting him is cut in the dub, but the mark it left on his face is left intact). What kid wouldn't be an emotional mess after all of that?
*** Even that's tear jerking (and somewhat understandable, if ''very'' extreme) if you look at it from Mrs. Kamiya's perspective; her son had just made a boneheaded decision that could have easily ended up leading to her younger kid ''dying''. What parent wouldn't feel the need to at least yell at their kid for something like that?
** [[FreezeFrameBonus It's hard to notice the first time you watch it,]] but look at Agumon while Tai is done telling the story. He's ''crying.''
* Takeru tricking Pinocchimon into thinking they were going to play, and then bailing on him. He probably thought he finally made a friend, but it wasn't so, and it was his own doing.
** What happens exactly makes it moreso; Takeru claims that Pinocchimon has no friends, so Pinocchimon goes off to prove him wrong by…building another puppet out of the junk in his house. While he's gone, Takeru destroys the things he used to screw with the other children. When Pinocchimon finally gets back to show off his 'friend', TK's gone. Something about the way Pinocchimon lets the other puppet fall when he realizes this...
* For some, [[JerkassWoobie Puppetmon's]] death.
-->'''Puppetmon:''' Cherrymon....what do those kids have that I don't?
-->'''Cherrymon:''' ''Friends''...
** Heck, you could probably consider Puppetmon's whole ''existence'' to be this. He's probably the most sympathetic Dark Master, because he just wants a friend to play with...the trouble is, he's a psychotic nutcase who's idea of fun involves killing and torture, so it'll never happen.
* Don't forget [[spoiler: all the Numemon teaming up against Machinedramon, only for all hundred or so to be killed with one punch.]] As a matter of fact, pretty much anything the Dark Masters do leads to this. Things like [[spoiler:Whamon being skewered and Puppetmon's BadBoss habits]] won't leave your mind easily.
* In episode 50, it's revealed that the Primary Village has been turned into a wasteland. Seeing Elecmon go from an overprotective JerkAss to a massive {{Woobie}} is quite a shock.
* Episode 51 had both Matt and Sora trapped in caves formed by the darkness in their own hearts. Matt, in particular, was angsting over feeling alone, thinking Tai was a better brother than he was. But Gabumon was able to pull him out of it by reminding him he wasn't alone. Even when Gabumon compares Tai and Matt to ice cream in the dub, the scene can still bring tears.
-->'''Matt:''' I've never let anyone ever get close to me before. Not since my family split up. Ever since then, I've been alone. I figured if my family didn't want me, that I would just keep to myself and never tell anyone what I was feeling, and I swore I would never let anyone see me cry. But, really all I wanted to ''do'' was cry.\\
'''Gabumon:''' ...Then cry.
** Gabumon even starts crying when Matt says that he doesn't matter to anyone, because Gabumon had been waiting his whole life for Matt.
* The last episode of ''Anime/DigimonAdventure'' and three preceding it. [[http://www.youtube.com/watch?v=eJkPyX4clMQ this makes it even sadder.]]
** To elaborate: [[spoiler: Palmon doesn't want to say goodbye, as she knows it's going to be too difficult; she even hides from Mimi as the latter runs through the forest searching for her. Some Geckomon, however, bring the poor thing out of depression by raising the point that not going to see Mimi off will be worse. So, later, as Mimi's crying on the flying tram car, Sora looks out of the window and suddenly shouts to Mimi to look out the window. And cut to the lone Palmon running, crying and shouting to Mimi. She's then joined by the other partner Digimon in a rousing chorus of Butterfly, acapella.]]
** In the English dub, [[spoiler: the ending music is changed to one final, full rendition of "Hey Digimon", which takes on a surprisingly bittersweet tone in the scene.]]
* During the arc with Piedmon, we have Joe's PapaWolf HeroicSacrifice to get Izzy to safety, which actually leaves Izzy in ''tears'' as he gets away. Even worse is the fact that it ''doesn't work'' and Izzy still gets captured by Piedmon immediately after.
* I am not sure if anyone else feels this way, but in the Digimon Movie when Wargreymon and Metalgarurumon get what looks like killed by Diaboromon and his clones. for those who have watched the entire series up until this point it is heart breaking to see them in such a state
* Meta example: [[https://en.wikipedia.org/wiki/K%C5%8Dji_Wada Kouji Wada]], Japanese singer who performed the opening theme "Butterfly", has passed away in April 3rd, 2016.
** On the English side of this tragedy, Paul Gordon who provided the songs for the English dub such as [[https://www.youtube.com/watch?v=1xDFWYt_pbY Let's Kick It Up]] also passed away on February 18th, 2016, just two months before Koji's death.
** On May 17th, 2016, Yuko Mizutani, the original voice actress of Sora Takenouchi, [[http://www.animenewsnetwork.com/news/2016-05-19/chibi-maruko-chan-black-jack-voice-actress-yuko-mizutani-passes-away/.102272 passed away from breast cancer.]]