I got a '73 5550, the filter should be up behind the radiator on the left side of the engine. An aluminum mount with two hoses and a spin on filter.
Our beasts don't have all the electrical solenoids and switches the newer 'gimp' qualified operator ones do, so it's probably a lip seal getting hard and not sealing in the cold. There are two clutch packs with apply pistons to engage the clutches. Cold plastic won't completely conform to the space and until the oil heats up and softens the plastic, no go....
Only other rubber or plastic in the tranny are some huge O-rings around the front pump which pressurizes the tranny, but those would be peeing oil, so it's back to the lip seals. Let it sit until it warms up, you don't want those seals to fracture. Then you get to split the tractor and rebuild the trans.
When I was learning about automatic transmissions 40 years ago, our instructor mentioned Chrysler had to install special lip seals in the cars and trucks sold around the Canadian border, north, and Alaska. There was 300psi to apply the rear clutch and that would shatter the seal. 5550 are seriously strong buggers, an oldtimer was watching me move some dirt with mine, he said to me that hoe will probably still be around and running when all of us are dead...