Rather than spam all the names on the Guild history post, was hoping one would come across here so I could ask a question. Actually, this could apply to all. I use to compete against a clan / guild in TFC (Team Fortress Classic) back in 99’ when I was 13 called something-something Old Timers. For awhile I thought it was this guild, but obviously I’m seeing that “we” were founded in 05’. I’m wondering if something existed before that, or if any of the original members recall a group that gamed with a similar name.
I’m not OG OTG, but I’ve seen many similarly-named guilds over the years. Some identically named…they just weren’t us. Then there are guilds with different names, but similar themes. I used to see The Older Gamers (TOG) a bunch, and I know they’re still around. Australian, though, so typically on at different times. 
OTG started out exclusively MMORPG related during the Dungeon’s and Dragons Online beta in Fall of 2005 - the start was about only 10 to 15 of us that started running around in late beta and realized most of use were in our 30s or older. OTG was maybe 60 people at the release of DDO in 2006. OTG grew immensely to thousands of members during the Lord of the Rings Online and Vanguard betas and release in 2007, but that’s getting nearly a decade after the time frame you’re thinking of.
Myth answered and I will derail the thread, but Team Fortress late 90’s, my start of PC gaming. Bought Half Life (Team Fortress as an add on to the CD Rom) and Baldur’s Gate for my new Gate Way PC. Out of college a couple years and wanted to something to do in my apartment at night. Good ole days, I played TF few a couple hours every night usually as a sniper. Then I discovered America’s Army and got a buddy to play. We used the old secretary head phones / mouth piece plugged into out landline phone so we could talk. Twitch Skills at my peak. So fun.
I found OTG in 2007 while geeked about Warhammer Online (so miss that game), Conan launched 1st and that was my 1st OTG MMO. Conan, Warhammer, Rift. We would launch with thousand plus members. The MMO hey day. Good times. Good guild times.
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I’m also going to derail, zeek, sounds similar to my story. I branched off to Dark Age of Camelot and Diablo 2 in the early 2ks, but late 90s I started my PC gaming with TFC as Sniper, joined clan as Pennywise (when I thought I played against a clan called Old Timers). Not long after I started playing Americas Army with a buddy from school. Pretty cool. It was definitely the golden years of gaming.
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