>>darkwa+(OP)
back in the '90s I was into connecting to IRC servers using spoofed IP addresses. The way it worked is you told the software what OS you were connecting to (or it would figure it out itself, I can't recall). Each OS had a unique way of generating TCP sequence numbers, which allowed the software to guess which number would come next.
Nowadays OSes have protection for this sort of thing. But I'd imagine you could still fingerprint an OS like that. Combine that with TLS, HTTP, etc. specifics and you could narrow it down quite a bit I bet.