I cried at the endings of all five seasons.

I would have to say the digimon Adventure ending, or when wizardmon died. *cries*

tamers ending,particually takatos speech at the end,its that hint of sadness in his voice i just wanted to see em get there partners back

Me, just finished Read Or Die T.V
Bleach and Naruto at the moment.
Soon to be Slayers, and maybe a re-watch of good old Trigun. I think it is a must to watch. If Trigun goes down well, then Love Hina.

When Matt is in the dark cave and he realizes that he does have friends who like him and really do care for him, as a kid without many friends it made me envious and sad I couldn't be like him so to myself I cried out of sadness of not having many friends.

Too bad I couldn't cry. I'm an apathetic dude.

But the closest would be the credits for the first Digimon Movie in Japan. It was when Taichi was standing with closed eyes and shown how much he and Greymon are bonded to each other.

The ending of Tamers, the ending of Adventure 02, and when Wormon dies.

There is a lot more but I can't remember them :[