Hi d2steph,
welcome to the BB.
Alas, to help you further we need a Serial Number as there are two models of Twenty Tractor.
The Small Twenty has a side valve engine and the Large Twenty has an overhead valve engine.
They can also be known as the Big Twenty starting at S/no's L1-up or PL1-up or the Small Twenty S/no's 8C1-up.
Main problem could be that there is too much clearance to where the clutch brake becomes effective--this would allow over travel of the release mechanism before the clutch brake engages, this action stops over travelling such as you describe.
Hope this helps.
Cheers,
Eddie B.