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Dungeon Siege 2, i couldn't believe it actually installed on Windows 7 when HoMM 5 didn't.
Post edited June 21, 2011 by Druidshinobi
Centurion, couple of days ago. I didn't have to actually *install* it, so don't know if it counts :P
And Dune few weeks earlier. I needed something to play on my netbook during flight.
Not really old, but the last one I think was Seal of Evil.
"What's the last old game you installed (and hopefully played) that isn't yet on GOG.com and roughly when was it?"

The original release of American McGee's Alice last week.
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serpantino: Title says it all really. What's the last old game you installed (and hopefully played) that isn't yet on GOG.com and roughly when was it?
Daggerfall and Deus Ex, last week.
Will be Morrowind later today,
Several, all today.

System Shock 1, Bioforge, Clive Barker's Undying, Project: Nomads, Thief Gold, Dungeon Siege and Nocturne. I own all of these legally and in physical form, which I suspect makes me mildly awesome to some people.
Delta Force. Haven't finished it yet. Got me a retail collection of Delta Force games all the way up to Black hawk Down Team Sabre.
Marvel Ultimate Alliance, not that old though. No One Lives Forever 2 retail that I picked up in a charity shop.
Indiana Jones and the last crusade, replaying it again
I installed Starcraft and Age of Mythology a little under a year ago.
Baldur's Gate 2 in November 2009 ( I know it's available here now, but it wasn't back then).

Diablo , Diablo 2, Icewind Dale and Half Life in Oct 2009
Post edited June 22, 2011 by CaptainGyro
Netstorm: Islands at War

http://www.mobygames.com/game/windows/netstorm-islands-at-war
Icewind Dale 2 about 7 months ago.

I found it at Amazon at 8$ and thought it was now or never.

In retrospect, I could have gotten it cheaper at GOG (once you include tax and shipping) and a CDless copy too.

Guess I should have googled around before committing to buy my Amazon copy.
Full Throttle via DOSbox, and not so old but not new either.. Street Fighter IV :D
Dungeon Keepr 2, (it crashes a bit but still playable) Wizardry 8 and System shock 2 are the last 3 games I installed that are not on GoG. Also had Balders Gate II and throne of Baal...and Planescape Torment installed but they are now available. Would love to see Warlords III Dark Lords Rrising available becaue I cant get that one to work under W7. Own the boxed copies to all of em.
Post edited June 22, 2011 by Byeohazard
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GhostQlyph: Several, all today.

System Shock 1, Bioforge, Clive Barker's Undying, Project: Nomads, Thief Gold, Dungeon Siege and Nocturne. I own all of these legally and in physical form, which I suspect makes me mildly awesome to some people.
Indeed, it took me 6 months of web-searching to find somewhere selling a new copy of System Shock 2 for a reasonable price. And that was 4 years ago. System Shock I is completely non-available these days...