Most Depressing/saddest Moment

[Jorah]

Trading a shiny Butterfree and Sabelye onto the same game, forgetting they're there and started a new game...

Funniest is probably my sister accidently starting a new game with her Golem on the old save file on Emerald and then on DP she ran into a shiny Geodude that Self-Destructed XD

 

[Valarauca]

When i found out you couldn't trade with 2nd gen games and 3rd gen games...

ITS FAIR I ONLY HAVE 20 LVL 100 LUGIAS!!!!!

 

[Taemin]

For me.. trading my Journey Across the USA Event Latias, and another rare Pokemon to a friend of mine, to help him in the Battle Tower.. Then as it turned out something happened, and I haven't seen him since to get them back. xx;

Oh, and having my Level 100 Pikachu from my original Yellow game, deleted by a friend.. on mistake, but it still sucked. ;~;

Now, for a friend of mine I had when I was younger.. he spend hours, weeks, and months on his Pokemon Red.. back in 1999. He was so hooked on that game, had level 100's of all his favorite Pokemon. Yes, he loved his Pokemon Red.. but then one day he went somewhere, and accidentally misplaced the game. Never saw it again.
He was too young at the time to buy another for himself, and his parents were upset that he lost his.. so he never got another, and that also pretty much ended his Pokemon obessesion, after awhile..

 

[World King]

Hehe. That's pretty funny... and stupid too. You shouldn't have saved it there. :P

My worst moment was when I was fighting the League for the first time in my life (in diamond) and lost to Cynthia's last pokemon. I was so depressed. Honestly, all that hard work of getting so far was lost. :(

Yeah, like THAT's real depressing. At least the E4 didn't move to Europe, so you faced them again and won.

 

[Satoshi-Ash]

1. When I caught MissingNo. in my Blue version , I tried to take it out of my PC, and of course the game froze. After I restarted the game, I was at Lance in the E4. But he was like, already beat. So I walked past him into Gary's room, the event where you automatically walk up to him didn't happen. I didn't bother talking to him, but intsead walked behind him to find a Lugia OW Sprite.(WTF?!) I talked to the sprite and what do you know, the game froze. Now every time I turn on the game I'm stuck there....

2. In my Crystal Version, I caught Suicune with the event, I caught Raikou south of Golden Rod, and I encountered Entei, multiple times... BUT I NEVER CAUGHT IT! :'(

 

[solopy567]

Very basic upset:

Found shiny Zapdos on FireRed, and i didnt have my masterball and i ran out of ultra balls...so...yeah

Also, back in GSC, i had a Togetic which was really strong and helpful...Lvl 100 too.
I put it in Box 8 for a while, and after some time it was gone!
I figured i put it in another box, but it wasnt there.

Apparently, the box was bugged and deletes any Pokemon i put into it, so i called it "Box of Death" so i would know which one it is

 

[Patchy]

I found a shiny Abra. It got out of the Ultra Ball with "Shoot! It was so close, too!"
Guess what happened...

I found a shiny Skarmory.
In the Battle Pyramid. ¬_¬

The shiny Starly I found was Rash. =(

Sapphire deleted itself. ;.;

 

[Shwicked]

Depressing moments...

My sister used my last Master Ball on a Poliwag in Gold.

I gave my cousin my Gold version (I had a lot of strong pokemon in it - especially my lvl 100 Typhlosion),and after a week later, I moved to Canada, and realized that I forgot to get my Gold version back. I was sad for a week.

Oh, and in Emerald, I encountered a lvl 80 Dusclops... in Battle Pike. T_T

 

[subaku]

Came upon and caught a shiny Raquayza (however you spell it), forgot I had it, proceeded to sell the game, and then realized in horror what I had done.

 

[Superjub]

Okay so I was playing Shiny Gold, and I was in Victory Road when I found a Shiny Ariados :O (I did not use cheats ;))
My brother said "Use an attack on it, it wont kill it." and poof, it's dead :(
But I found a Steelix in Victory Road (Again Oo) which was shiny on Diamond so I'm happy ;)