Windows totally does, at least in my experience. I'm not installing software from "questionable" sources or downloading random executables from the internet, but Windows pretty consistently develops problems like several seconds of progress bar to load local folders.
YMMV, but that's been my experience on every Windows computer I've had, including Windows 7 and 8 on SSDs. Surface isn't showing signs of it yet, but that's only a few months old.
That definitely was my experience pre-Windows XP. Windows XP made it "better" and Vista "solved it."
There are things I can do to make Windows slower (e.g. Installing VMWare/Hyper-V w/virtual network adapters), running out of drive space, running out of RAM, bad Windows Explorer shell extensions, or just multi-tasking too heavily (e.g. 30+ Chrome tabs left open for days).
But in general I haven't noticed much natural degradation I cannot pinpoint the source of like the old days.
I'd be interested to dig into your system to see if I can determine the source of your "slowness." Normally the performance tab gives some clues and if not Process Explorer with the DLL display can find others. The Event Logs occasionally have information if it is hardware, COM, or service related.
Definitely not disk space, RAM, or too much multitasking, but it could be shell extensions (don't think I have anything unusual) or virtual network adapters (VirtualBox, Evolve, and Viscocity). Never gotten any clues out of the performance tab, but I didn't know about Process Explorer until a few months ago. I'll definitely take a deeper poke at it if it shows up again.
At least the days of LAN parties invariably starting with someone wiping their computer to fix a networking problem are done with!
Windows 8.1, OS X Mavericks, and Ubuntu 14.04.1 LTS certainly don't. They also all support TRIM or defrag depending on storage.