Code Geass, second season... Don't want to spoil it, so I'll just say the anime was grand and it couldn't have ended in any other way, but still it was way too sad for me back then.
The first show to make me cry was Elfen Lied. Well, it was the first Anime that I watched other than Dragon Ball Z.
I found AnoHana quite touching, too.
Maybe it was because of my age at the time, but Doraemon has had several epic tear-jerking moments.
The climax of "Goodbye Doraemon" as well as the seventh (original) movie 鉄人兵団 come to mind. There are of course many others, and most of the original movies have at least one part that will get you emotionally charged (which makes them so great!).
I know it's not canon, but the fan-made ending to the series (the good one) made me cry a bit too.
Hello, there seems to be something wrong with the file you uploaded. The game works fine, but it doesn't play music. I use dameon tools lite and prompt "unable to mount image. Cue sheet: line 1-file not accessible." Could you please re-upload it?