John Deere Oil

Possibly a cracked case between the trans and engine, On things like this I use a shop vac on "blow" mode and stick it into a fill hole, use soap and water mix to look for the leak. In your case or situation I would drain engine oil,remove top cover stick the vac into the trans fill hole (you can size it with tape), then start looking for the leak.
 
Just finished restoring my 1949B had the same issue, when i tore it down i found out that the cover for the pto bearing behind the first reduction cover was broken in half letting the fluids mix
 
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