They don't have perfect seals, but should take more than a couple minutes to drop.
Chances are the seal rings and cylinder are galled and leaking. You can look in through the inspection covers for fluid leaking down from the cylinder. It can also be blown orings on the standpipe.
Changing the piston and cylinder requires lifting the top cover. Best have a shop manual before attempting this. The cover is heavy, the control linkage extends all the way down to the pump controls and is delicate, easily damaged. You will need some means to do a controlled lift and know which bolts to remove.
Chances are the draft link boot will need replacing, be a good time to do that if you go in.
Unless you need the lift, be easier to just chain it up when not in use.
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Today's Featured Article - Upgrading an Oliver Super 55 Electrical System - by Dennis Hawkins. My old Oliver Super 55 has been just sitting and rusting for several years now. I really hate to see a good tractor being treated that way, but not being able to start it without a 30 minute point filing ritual every time contributed to its demise. If it would just start when I turn the key, then I would use it more often. In addition to a bad case of old age, most of the tractor's original electrical system was simply too unreliable to keep. The main focus of this page is to show how I upgr
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