1, My Little Dashie

2: I couldn't wake you, because you can never wake up again...

3. Decay

4.MLP: Friendship is Tragic

5. Where all roads lead

6.Magic Never Fades Away

7. Pretty In Pink

8. The Last Crusade

9. End Of Ponies

286609 No, that deserves the #4 spot, if not higher up on the ladder.

With the addition of the story I'm adding, I think this should be the list.

1- Not all who wander are lost
2- I couldn't wake you, because you'd never wake up again...
3- My Little Dashie
4- The End of Ponies
5- Pretty in Pink
6- Decay
7- Eternal
8- The Last Crusade
9- Where all roads lead
10- Magic never fades away

Never read MLP: Friendship is Tragic, so I didn't count it in my list.

Where's the link for Decay?

I'm writing a story that could make this list in the future. It's called Fading. Look out for it.

-Imagewicked

Not to be a self-promoting pompous ass, but...

Could The Pony in my Pocket be considered a sad story? Or a bittersweet one?

I came here because there was a link on my dashboard leading me here, though I have no idea why

I'd say the fics that made me sob the loudest were "Pretty in Pink", "To Be an Alicorn" and "Final Dreams of a Filly". Especially the last one has me tear up every now and then when I think about certain scenes

I gotta be honest though, and I know a LOT of people disagree with me but: I didn't find My Little Dashie to be all that sad. Sure it was sweet, and rather moving, but I didn't like the writing style and the endless use of that "my heart exploded". It was like it was trying too hard.

#5 has to be "Just keep Laughing", that story is amazing.

Lunacy

Bittersweet was pretty sad.