If your shifting mechanism is all in good condition and this still comes out of gear probably the teeth on the gears involved are worn from grinding into gear. The teeth get chipped/worn so they have a small angle to them that, when power is applied, causes them to slide apart. I haven't seen this in a Cub specifically but in other transmissions. If it isn't a transmission with sliding gears then the "dog" teeth that engage get worn the same way from grinding and cause the same problem. If the shifting fork and shifting mechanism has to hold the gear in position under load it will wear out the shifting forks as they are not designed to hold gears under end thrust, just to move them. When in position they should not be moved by the power flowing through them which worn teeth can cause to happen. This wear can be very slight and difficult to see. It can look like a taper on the tooth from one end to the other. Or on "dogs" the engagement surface will be rounded off and then slightly tapered. Both cause end thrust to the gears which cause them to move and overcome the slight resistance of the shifting mechanism and them "pop" out of gear. You do want to make sure the shifter is working right and shifting it all the way into gear.
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Today's Featured Article - 12-Volt Conversions for 4-Cylinder Ford 2000 & 4000 Tractors - by Tommy Duvall. After two summers of having to park my old 1964 model 4000 gas 4 cyl. on a hill just in case the 6 volt system, for whatever reason, would not crank her, I decided to try the 12 volt conversion. After some research of convert or not, I decided to go ahead, the main reason being that this tractor was a working tractor, not a show tractor (yet). I did keep everything I replaced for the day I do want to restore her to showroom condition.
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