TO 20 transmission sticks in first and second gear

My TO 20 sometimes sticks in first gear so hard that I have to use a cheater bar on the shifter to get it out of gear. Sometimes it bends the gearshift. I bought the tractor from an estate so I don't know the history of it. The gearshift has been welded several times by a previous owner. I only use this tractor for running my dyna-balance mower. It has been mounted on the tractor for the last three summers. I never use this tractor for anything else. This tractor has a Hupp over/direct/under. I don't know if that will make any difference. When I bought the tractor the transmission was nearly empty as the oil had leaked out past a loose lift link mounting bolt. I don't know if it leaked out during the several years it was parked or if the previous owner used while it was dry. The tractor serial number is in the 43xxx range and the transmission case is cast iron.

I was able to stop the leak by tightening the lift link mounting bolt with an impact wrench.
 
I have a TO30 which is similar but not the same. I admit from the top that this is a long-shot idea, but I thought of it as a small possibility when I read your question.

I occasionally have real trouble getting my tractor out of first and sometimes second. But mainly when using the 3pt or PTO--heavy weight on the 3pt seems to make the problem worse.

If I drop all weight off the hitch, or if I disconnect the PTO, it will shift out of 1st easily again. Or, if I just every so slightly engage the clutch while trying to shift it will slide easily out of first.

So, like I said, this is a real long shot. Is yours the same with the PTO engaged or disengaged? And if you are trying to pull it out of gear and just barely engage the clutch does it make any difference?
 
It could be rust related.

Those are known for collecting water in the transmission. If the shifter boot is bad or gone, and it lives outside, then it will have water in the cases.

Even a little water will condense in the upper portions and keep the shift mechanism wet and rusty.

Might ease the top off, see what's in there.
 
Well?
The wife's Fergy has a Howard and Hupp. I am trying slowly to add an Everett to it.
48 forward gears, 12 reverse, might be fun.
Currently 12 and 6 is a good start.
 
Thanks to everyone for your help. I will try the suggestions when I cut my last crop later this Fall. I won't tear into it at this time. I am currently driving about 280 miles each weekday for cancer treatment in the city. That doesn't leave much time to tinker as my shop is the great outdoors and the days are getting shorter. I do have another gearshift and cover assembly to put on but I don't think it will help. I would like to find a Ford 8N to put the mower on. I grew up using this same mower on an 8N.
 
Keep Kicking! I did the cancer routine a few years ago. Second round of Chemo about did me in. ALWAYS Maintain a sense of humor.
If going through radiation thank them for making you glow. Especially at night. That way you no longer need a flashlight.
If the hair all falls out you are now aerodynamic. You can now swim faster also. Stocking caps folded up like a Mohawk hair cut can just about regulate your head temp. If going through surgery, tell them its a great weight loss plan.
Best of luck! God Speed on a rapid recovery.
 
Not doing chemo at this time. I do mention that someone needs to bring the barbecue sauce. I still have 3 weeks of treatments.
 
So your getting the night light treatment then. You should thank them for making you self illuminating. Ask them if they will give you a mask to cover your eyes so you can sleep at night.
Best of luck! Godspeed on a recovery!
 

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