First, what Ron said. It's typical of a lot of old tractors, but I always called it the Farmall crunch. Give your driveshaft time to stop after pushing the clutch pedal, and you'll have a lot less grinding when putting your Cub into gear.
Is the grinding on the left side in all gears? (Part of the problem is that the tranny is on your left, so it's hard to narrow down whether it's in the tranny or the final drive.)
If not, is it worse when pulling against the gear than when coasting against it? Or the other way around? Does it pulse at a given speed? Would it be better described as a groan or a howl? If so, it's more likely wear on the faces of a gear from a lot of work. Not a lot to do about that except replace the gear, which is a BIG job and may not be worth it.
If it is more of real grind and happens in all gears, regardless of under load or not, and the noise is fairly steady for a given speed, it is likely a bearing. I'm not sure how to tell you how to nail down which one it may be but there are four, I believe. One comes out of your transmission/differential. The next, is just outside of that where the differential shaft goes into the final drive. The other two are on each end of the shaft on your bull gear in the lower part of the final drive. All are ball bearings, and it could be any one of them. It's also possiblethat, if it's the bearing that mounts in the tranny case, that you popped a ball out of it that's fallen into the tranny case.
You might want to check out a couple of the Cub specific sites for some guidance, too.
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