Well there are a couple of solutions for this, at the end the strategy is doing a lookup, and then an eval applied.
But the better one is to configure an automatic lookup for this to enrich the data with the Host_Operating_System field from the lookup and so when you search it it already comes like this:
Assets, WindowsVersion, Host_Operating_System
Asset1, 2003, 2008
Asset2, 2008, 2003
Asset3, 2012, 2012
And then you just have to do and eval if(WindowsVersion=Host_Operating_System, "Yes", "No")
Check this link on how to create an automatic lookup
If you dont want to alter the index's harmony, then do a lookup on the asset and an eval
index=foo sourcetype=bar | lookup fooAssets.csv Assets OUTPUT Host_Operating_System | eval Difference=if(WindowsVersion=Host_Operating_System, "Yes", "No") | table _time, Assets, WindowsVersion, Host_Operating_System, Difference, _raw
Regards,
Rafael.
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