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It really depends on the game.

One that I want to give thumbs up in particular is Age of Wonders (https://www.gog.com/game/age_of_wonders). It's a 2D turn-based strategy that was released in late 1999. Even back then it was unusual in explicitly supporting Windows NT, and perhaps that's why it continued to work just fine with 2K, XP etc.

But what's even more interesting is that they made the UI to resize according to the resolution, and resize it does - it supports literally any resolution (I tried it on 4K!), and it will properly resize everything. Of course, the widgets and the fonts are still bitmap, so everything's tiny - but even so, still impressive.

All in all, I'd say it's a good example of Win32 API stability. Windows upheld its part of the bargain, and a game like AoW that used all those APIs (DirectDraw etc) strictly as documented still works. The ones that don't work are generally the ones that made assumptions that were valid then, but no longer are.

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