When, after literally hundreds of times trying, I destroyed my older brother playing Warcrat 2.
He was so pissed, he closed out of the game just before it ended, told me I'd cheated, and wouldn't accept defeat. I didn't cheat, I just saw a gaping hole in his tactics. Haha

Well, despite being only 31 years old I will sound like a boomer like now, but both my proudest gaming moments come from 2006-2007. In 2006 my PC went down thanks to aa lightning strike next to our house. My brother was very kind, and left his laptop at home so I can practice programming. It had FreeBSD operating system, but I was able to make Flight of the Amazon Queen run. Ot was a pixel graphic point'n'click adventure game, the only game I was able to get and play at that time via SCUMVM (we didn't have internet at our home for 2-3 years later). I was so proud when I've beaten it without any walkthrough (again, no internet and none of my friends played it). The second one was a year later, when I've got a used PC and beaten the campaigns of HoMM3: Armageddon's Blade, which I've found impossible when I was younger. Also Abe's Exoddus and Oddossey, rescuing all mudukons were very hard and satisfying.

From the past years: beating Shadow Tactics: Blades of Shogun, 7th Sector, Memoria, challenge running Might and Magic X with full mage party on insane, finishing the Deponia quadrology, beating the water tree level when still learning how to use a controller in Ori, all those were very proud moments.

Thank you for the giveaway dear GOG staff.

GOG community is the best on internet and most generous.

My proudest moment was beating the entire Witcher 1 and 2 games on hardest difficulty and giving happy ending to all the characters in the all of the main quests and side quests.

I have yet to play Witcher 3.

I am in.

Back in 1994 Bethesda initially released their first Elder Scrolls game, TES: Arena in a broken state. Having bought the game here in Europe at a computer convention as a strapping young lad later that same year, that meant that at 80% in, after spending dozens of clueless hours playing the game after school, the main quest required me to visit a location that simply didn't exist in the gameworld at all...and so I couldn't continue playing it (technically you can spend near eternity playing the game -if you can stomach it- but the main quest is the only quest that isn't generated on the fly). Sure, Bethesda were quick to patch and re-release on CD-rom IN THE US at the time, but this was 1994, and for me there was no such thing as a games store, a BBS scene, (expensive imported) games mag demo disks with random patches, let alone the WWW internet. I ARJ-ed the game to 3,5" diskettes to get the resource hog off of the HDD, maybe try again later and so the years (well...decades) went by.

In January 2018 I had to take my dear mother's wheezy 486DX2-66 PC out of storage to retrieve some old Word/WP files, so I put it together on a dining table, managed to convince it (through hard manual labor inside a jungle of unmarked PCB's and weirdly flat cables) to post and boot, and decided I would finally replay TES: Arena on it, except now with that 'new' patch installed. I quickly discovered that the 9 volume ARJ-ed '90s copy containing my old savegames was missing a disk or two, so I reinstalled from the good-as-new original game disks, RTFM-ed on the loo, and started from scratch. Gazing at the (at time of release already iffy) blocky, tear inducing VGA graphics on an ancient 14" fishbowl CRT. And using a quarter century old, dirty ball mouse (oh joy, I still have a spare twin for that thing...imagine the loss if it were to break). After a couple of days runtime the weird smell from the decades old, leaky caps on that 1993 486 motherboard had finally dissipated, but the game's tunes started to haunt me whenever I wasn't playing. I re-explored those dungeons, figured out the answers to the game's sometimes frustrating riddles to eventually reach previously left untrodden paths and before February 2018 had arrived, I had finally finished TES: Arena's main quest. After nearly a quarter century I had righted a wrong and finally gotten my money's worth. So yeah, Bethesda and their infamous bugs: the long, long version. I copied a working savegame (quarter century old 3.5" diskettes are even worse than brand new ones were a quarter century ago) to a more civilized WinXP system (w 3.5" drive and USB that also happened to have had Bethesda's own freeware release on it the whole time, BTW, just couldn't be effed to play it that way). As proof that I had finally done it. And in style. Just to finally scratch that itchy Arena from the list and erase a bad childhood memory (well OK...mild frustration) at the same time. And I guess I have to admit I'm sort of proud of that...

My favorite accomplishment has to be winning a game of Halo 3 at a LAN party on launch night, despite not having owned an Xbox or a Halo game before then (my only experience was playing at friend's houses).

When I was a little kid I was proud to have beaten Street Fighter Alpha 3 in the arcade, but that game is ridiculously easy compared to Super SF2 Turbo...

I was playing pathfinder knigmaker's varnholds lot dlc and I was stuck and I actually had to use all the potions, scrolls etc that I normally hoard and never use and I was so happy that for once in my life I had to use ALL of my items to complete the dlc. Honestly my proudest moment in gaming.

One of my moments of gaming glory was when In 1992 I learned how to do a dragon punch with Ryu and Ken in Street Fighter II; The World Warrior for the Super Nintendo. I wasn't that great at sports so my brother and his friends would use a low hoop basketball rim to dunk on me and then tell me to go back in the house and play street fighter. Once I learned how to use the invincible dragon punch I practiced it so many times I got blisters on my left thumb. Shortly after that almost no one wanted to play me in Street Fighter II because I would just Sho-Ryu-Ken the shit out of em' and it only got more fierce and fast when Turbo Hyperfighting came out.

Beating Final Fantasy III on the SNES for the first time is my proudest gaming moment.

The entire game was so moving and profound. I became emotionally attached to all of the characters and the world they lived in. Beating the final boss, with that incredible music, was the epitome of epic.

I cried several times during the 30-minute-long ending. When the end credits finally stopped rolling, I was left with a deep sense of emptiness and peace. This experience inspired me to become a video game designer and move from Michigan to Los Angeles to start my career in the industry.

I've been playing games since the mid-1980s, yet this is still the strongest memory I have of any game.

My proudest moment has to be finishing Spider-Man 2 on the PS2. The PS2 was my first video game console and Spider-Man 2 was my first game, I got them both for my birthday when I was seven. It was by far my favorite game I played when I was little but I could never beat the boss fight with Rhino so I never got around to finishing the game.
I graduated high school eleven years later, in 2017, and while I’m hanging out with some old friends that first Summer out of school we start talking about our first games we played. I get all nostalgic so when I go home I boot up my old PS2 and put the game in. My old save is still in there, and it’s just before the Rhino fight. I load it up, and beat it on the first try.
Afterwards I pause the game and just sit there for a moment because I’m giggling like an idiot. I probably put about sixty hours into that game when I was little but gave up because I couldn’t finish that one fight. I spend that weekend finishing the whole game. It honestly felt like I had just beat an old bully from my childhood, and that is now easily one of my fondest gaming memories.
I’m twenty-two now and I think that whenever I have a kid I’m going to give them that game and console for their birthday when they’re old enough. It’ll be nice to let them appreciate the old stuff before I get them a PS9 or something.

My proudest moment was finally dodging 200 lightning blots in FFX to unlock Lulu's onion knight abilities. I was so nervous that I had miscounted that I just kept going and made it to 247

I played many games after 25 years of gaming and had many good moments so this is a hard one but, there is one moment that sticks out for me.

This was in Dota 2, so I was playing solo hard lane Lone Druid wich is one of the hardest heroes in the game but he is very powerful when you master him and his bear companion. I went solo to my lane and was against 3 enemies they killed me for first blood naturally I was pretty pissed and tried to funel my rage into getting my revenge, so when i respawned and got back they get even more cocky. I fought them 1 vs 3 and managed to kill 1, but they dont back down. I juked the other 2 running from them in the trees while my bear is just mauling them in their moment of tunel vision, killing 1 more and at the moment of his death there comes their midlaner giving chase to me. I managed to get to my tower but they still wouldnt stop so I slaughter all 4 surviving on 7hp(1%). They rage quit the game and I remember that I'm recording lol.

Got it on youtube, the video is called "How to gank Lone Druid."

beating bloodborne

Having the fortitude to beat Kos in Bloodborne is my proudest gaming moment.

My most recent proudest gaming moment is finally beating Gabriel Knight Sins of the Fathers. I had gotten pretty far back in the 90s but I never could get past those annoying zombies in Africa I finally figured out what I was doing wrong after years and years and successfully finished it and saw the awesome ending.

My proudest moment is probably when I beat the original Castlevania on the NES without using save states. Granted, I only could beat it by spamming holy water, but it was still pretty hard.