There probably isn't a way to determine exactly when each first went into service, but you can estimate it. A lot will depend on the OS in use, and the way the systems are used and managed.
One thing that might tell you a lot will be the creation dates of directories in the Windows Profiles directory. (In Win-2K it's C:\Winnt\Profiles).
On mine, there is an "All users" folder created on 5/4/2001, which is close to the time when I first got the system set up and working properly on the office LAN. I actually got the system in late April, but it took a week of installing and reinstalling apps., Service Packs, and a few changes to my account to get it set up properly.
The C:\Winnt\system32 directory, however, shows a creation date of 3/21/2001, which is about a month before I ever got ahold of the system (I assume this is when the factory install of the OS occurred).