I have this happen to me sometimes with gear drive Cubs and larger tractors too, I usually let the clutch up ever so slightly to get the drive shaft to spin just a little bit, then just before it stops spinning, gently try putting it in the gear I want. Doing this you can "feel" your way into a gear. I must emphasize doing this GENTLY, do not try jamming it into gear or you will damage the gear teeth.
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Ian
Mine: 72 w/ k301, 3 125's, 1 w/ hydro lift, 38,42, & 2 48 decks, 2 42 front blades, QA-36a & QA-42a thrower, tiller, lo-boy 154. Also, LOTS of parts.
family's:2 105's, 2 106's, 149, 2 lo-boy 154s, Farmall Cub.
Non-IH: 1940 JD Model A, 1954 JD 40 U, 1955 JD 40 Crawler, 2 1956 JD 420 U's, both w/ Henry Loader and Backhoe. JD 110. Wheel Horse (model unknown.) Power King 1614. We love our tractors! 
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