[nothincomin825]

Which would form the greater enolate in acidic/basic conditions and why?

2-cyclopentenone or cyclopentanone?

My answer is 2-cyclopentenone because of the double bond making the alpha hydrogen (proton) much more acidic compared to the hydrogen on the cyclopentanon. Am I correct or incorrect? Thanks

[Schrödinger]

I think the answer is 2-cyclopentanone in basic conditions. But I believe your reasoning is incorrect.
Try the hydrogen that is not attached to the sp² carbon. See if you can find other factors that stabilize the enolate.