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So maybe you're thinking "wait, we've seen this" but this is slightly different.

This is Advent Children Cloud vs. Crisis Core Sephiroth.

So can Cloud at his strongest defeat Sephirotha t his weakest fairly?

Wasn't Sephiroth toying around with First Class Soldiers even then?
Also, in Advent Children, Cloud was getting schooled by mere aspects of Sephiroth. Him beating Sephi in their final battle was simply an example of the "Hulking up" routine.
IMO, Cloud beating any Sephiroth is PIS. He lost, only to have the writers state that "He wasn't exerting himself". To rephrase, he was deliberately getting his @ss kicked. LOL.

For this match-up I'm routing for Cloud at his peak beating Seph at his weakest.

Cloud.