Try:

"Us humans are so limited in our capabilities. I'm willing to admit, in many ways, I run slower than Windows 95. God, I'm awful at jogging."

Running is the connection here, that's clear. But it seems to me that jogging should be the punchline, not Windows 95. Win95 works as the setup. Maybe I prefer that because Win95 is a much more specific thing than jogging. The punchline "I was talking about Windows 95 all along!" just feels so arbitrary compared to "I was talking about jogging all along!"

There's also a bit much lifting done in your punchline (double meaning of run + bringing in Win95), but even when you disjoint the two a little more, it doesn't work that well:

"I'm awful at jogging. I run slow... I'm not even the Windows 95 of joggers."

Windows 95's start menu was drastically faster than Windows 10's with its default settings. Things like that mean the joke just results in thoughts like "By what metric?" and "Was Windows 95 ever considered famously slow?"

Or is the point that the reference doesn't need to be accurate but just has to catch a general vibe of "old = slow"

I think it's at least three things:

1. win95 has waning cultural relevance, and nobody has any fresh memories of dealing with its slowness

2. most of us have seen "windows bad" jokes a million times over by now - it's stale

3. "run" is a pretty weak/generic connection.

Edit: 4 - "I'm bad at running" has a sort of boomer-humor vibe to it, it's less relatable to an audience that's generally in-shape.

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