IMHO, yes. Others have done it and are quite happy with the results, though.

To me, the bigger tires just soak up too much power, and a Cub has little to spare. They also increase the ground speed, which in my opinion is too fast in 1st and 2nd already. They also look too big on the tractor IMHO.

Personally I would prefer 7.5x24 but the tractor runs uphill.
 
9.5 was the standard tire on the later Cubs. All you can find reasonably now is 8.3 and 9.5, not that much difference.
 
I have 9.5 on both of mine and have no trouble either mowing or cultivating in 2nd gear on either one. Mower although is a woods 42 don"t know how good they would do with anything bigger.
 

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