Apple Dual-Link DVI adapter doesn't work after upgrade to 10.9.2
I would probably install the old OS onto an external USB drive to be sure it's not a failure unrelated to the OS.

It's rare that the OS breaks an adapter that was working - even if the change happened at the same time as an OS update. Also, you can usually rule out software by updating to 10.9.3 (in your case) or to the next point update in case there was an error that was caught in the drivers or settings.