Winning in this context does not necessarily mean vanquishing your nemesis. OSS can win simply by becomming a viable, usable alternative in a healthy, diverse market. Not long ago, the prize of mere coexistence a fantastic notion...for any non-Microsoft alternative. Apple was hanging on by their fingernails, too.
If 'OSS' wins, that doesn't mean the end of competition. Rather, it means the beginning of competition between the numerous distributions, window managers, package managers, etc.
Fortunately, these are almost all based on the same kernel, which will allow for better interoperability and cross-platform software (cross-platform meaning Ubuntu/Red Hat/BSD/Mac etc, not Windows/*nix variant). OSS is a philosophy, not a monopolistic party.
Or, possibly, the beginning of an Apple-dominated monopoly.
I think the competition between proprietary and OSS is more productive, as Windows/Mac and Linux complement each-other better than two Linux distros would for example.
Furthermore, there are interesting features/research opportunities that simply aren't interesting for either single party.
In my experience the kernel is not such a big issue when it comes to cross-platform software. In fact, having a cross-platform core is doable right now with reasonable effort.
The problems are ironically related to the different desktop managers, package managers and so on. :)
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