That's an old ASDM (ca. 2008) and I haven't had the opportunity to try that specific combination.
In general, modern ASDM versions (6.4 or higher) are documented in their release notes as being compatible with Windows Server 2008.
As long as your ASA is 8.0 or later, there's no reason not to load and use the latest ASDM (7.1(5) is current as of right now). That's actually recommended by Cisco.
