You have to pop the top to get at it. It might be the bearing at the front of the shaft full of gears. My H had a bad spring that holds it in gear and worn teeth on the gear itself. Those are the top three causes.
 
No need to split the tractor. You may be able to get at the problem by just removing the belly pump, clutch shaft and belt pulley gear assembly. You should be able to see what is wrong by just removing the belt pulley gear box, as that will expose the 5th gear set. Most likely, the internal teeth on the 4/5th sliding gear are worn to the point that there is not enough gear surface for it to stay in 5th. 5th gear drives straight through the top shaft to the differential. It will be an easier job to replace that gear if you also take the top cover off the transmission. It is very heavy and you will need a lifting device to get it off.
 
(quoted from post at 06:53:15 04/11/11) No need to split the tractor. You may be able to get at the problem by just removing the belly pump, clutch shaft and belt pulley gear assembly. You should be able to see what is wrong by just removing the belt pulley gear box, as that will expose the 5th gear set. Most likely, the internal teeth on the 4/5th sliding gear are worn to the point that there is not enough gear surface for it to stay in 5th. 5th gear drives straight through the top shaft to the differential. It will be an easier job to replace that gear if you also take the top cover off the transmission. It is very heavy and you will need a lifting device to get it off.

Can you pull the shaft from the belt pulley hole? That would save A TON of work.

I think on some models you can change that front bearing without popping the top. Not sure if there is enough room on all of them. I had the top off when I did my H so I didn't even try. Also, I always forgot about inspecting 5th through the belt pulley because I went in my H for a broken differential carrier and happened into the bad 5th gear.
 
You can pull input shaft which is the front half of 5th gear from underneath but to get the other half of fifth which is also fourth you have to pull cover. Make sure your detent is good and strong. Those springs break . If your gears don't look too bad I have put a spacer behind the rear bearing of input shaft to move it back farther for more engagement. You should add equal spacer underneath heavy washer that holds yoke on shaft or washer will have too much bend in it. Kind of have to figure things out as you go when making modifications such at this. Hard to find good gears now days though. I have a couple pretty good 4 th 5th sliding gears but I don't think I have the input shaft part.
 
The input gear and shaft come out through the front of the transmission housing after you have removed the main shaft coupling in front of the transmission and the clutch shaft. You unbolt the carrier that holds the bearings and seals and pull the complete assembly out. I think this would allow changing the 4/5th slider gear through the belt pulley housing opening. Anything else and the top has to come off the transmission.
 

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