Sometimes I have to double clutch to get my 1991 Cherokee Sport 4.0 to shift. It is always a little rough, but sometimes won't go into gear and I have to pump the clutch and it will go in. Also, sometimes when I start the Jeep, it is like the clutch is not all the way engaged and the truck will jump a little.

fix the clutch hydraulic system
check fluid level in reservoir
bleed the clutch system
fit a new clutch master cylinder

Could be the clutch.
Reverse and first do not have gears that line up like the others do. So if the clutch is not disengaging all the way, they will grind.

It might work short term, but it sounds like the overdrive might almost be out of your truck.

Usally when the clutch is bad, you still can shift gears. Check the slave cylinder or air in the fluid line. Good luck

"The shift pattern is a little different, with reverse starting to the left of first, in the German (Getrag in this case) pattern rather than the "reverse-in-sixth" Japanese pattern. It's nearly always easy to find the right gear, though sometimes reverse can be tricky (presumably this gets easier with time)." from a review I found , hope it helps. I suspect reverse is up and to the far left R 1 3
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2 4

clutch self adjuster is bad,you need to replase cabel/try orileys auto parts first,or dealer for cable.
tim

I am dealing with a very similar issue on my 03 Spec V , So far i noticed the clevis pin was loose and the locking hitch pin that slips thru it had fallen out . this caused the gears to not wanna engage due to the bolt behind the clevis which runs to the master cylinder was not getting pressed in when i pushed the clutch pedal in because the clevis pin was slippin on n off giving me no pressure up top .. I had to remove my lower dash panel in order to get visual n hand access to this pin , it is a tight spot to work in as well . May be easist to remove the 4 14mm bolts that hold yur driver seat in to give ya more room to work n stretch out ur arms

Reverse clutches are burnt. Clutch material is getting into valve body causing late shifts since valves can't move. transmisison will have to be overhauled. wish i had better news. sorry

try double clutching(come out of 3rd then push clutch twice b-4 going to 4th. if this works your clutch slave may be weak or pressure plate is worn. Try shifting from 1st-3rd if engine revs like your in neutral replace clutch. when going 1st-3rd engine should catch and cause vehicle to buck&stumble. (check level of clutch master cylinder)