The two most talented fighters in history (honorable mention to Floyd Mayweather Jnr) clash at Middleweight. What transpires? I say Roy wins a close unanimous decision over 12 rounds. Over 15 rounds he still wins but by 1 round.
I have to pick Jones too, although Robinson's power can turn tables against almost anyone. Jones' edges in speed and movement would decide this
I dislike Roy, but I've got to give it to him here. Too big (Sugar Ray came in at 157 against Light Heavy Joey Maxim), too fast and I think his chin was actually very reliable in his younger days. If anybody could have caught Roy, it would have been Robinson........but I think his reflexes are good enough in his prime to roll with the punches better then Fullmer and other guys when they got caught. I have Robinson Lb. for Lb. #1 by a longshot, but he was not close to invincible at Middleweight. On the other hand it's awful hard to be when you're fighting a dozen times a year, many of those on the Championship level.
At 160, I think Jones, although not was complete certainty. Size and Robinson's relative unfamiliarity with how much Jones would make him lead the action seem the deciding factors for me. That's one thing modern fighters have over guys from the 50s - a greater willingness to stand about and let the air fill with stink rather than fight if it gives them an advantage.
The pre-retirement Robinson gives him hell. But at 160 Ray wasn't the same animal he was at 147. Roy wasn't at his peak either at 160 but he had the speed advantage and he wouldn't stand in front of Robinson to allow himself to get hit with the left hook.
I think the pre-retirement Robinson tends to get highly undersold at 160... he was still extremely formidable... To me, it's a pick-em... Jones certainly has the right style to give Robinson problems, but conversely Robinson would also be the msot offensively gifted fighter Jones ever fought, I think that is significant.