I agree with the above however you may want to check the oil level on your dipstick to be sure it's correct. You could have diesel or hydraulic fluid getting into your oil. If so that's another situation needing addressed.
Right-O. All good advice. Oil is leaking past a seal and collecting in the bell housing. The oil is either coming from the engine or the transmission.
You are probably looking at splitting the tractor and replacing one - or both seals. They are not difficult. This is a simple job. A lot of unbolting, and supporting, but nothng technically tricky. At my shop we loved these jobs for young mechanics. Estimates have a way of being wrong, but without problems this is a 85% labor and 15% parts cost type of job. In a shop it would take one full day. As a home mechanic it will take every evening for a week - plus the weekend - depending on what kind of wheeled supports you can rig up BEFORE you start turning wrenches. After all, you are about to have two halfs of a tractor but neither end supports itself
But first check both oils to make sure that neither the engine or transmission has too way too much oil in it. There is a chance that the oil seals are good, but just leaking because one or both are under oil instead of being slightly above the normal oil level. And also check the weep hole at the very bottom of the bell-housing (where the clutch lives). Oil that naturally builds up in the bell-housing should be able to drain out the weep hole at the bottom. A typical weep hole is at the lowest point and is a quarter inch hole with a loose cotter pin kind of stuck into it. This is so you can wiggle the cotter pin to dislodge any dirt and crud allowing trapped oil will pour out.
As far as damage to the tractor, there probably isn't any. Too much oil will make the clutch slip and can even back up into the starter and make it fail. But when you split any tractor you usually replace the clutch friction parts anyway - not expensive - and the starter can simply be cleaned out and be fine.
rScotty
The big danger is the same as any oil leak - that you will forget about it and run the engine or tranny out of oil.
So pay attention to that.
luck, rScotty