TNG was great. Best of Both Worlds two parter episodes amongst others were my favorites. Watching the Borg Cube pass right through the Mars defense missles (with that heavy paced drum music).. it used to give me chills when I was a kid.
There was a comparison once that a star destroyer tactically would lose to the Enterprise, because of transporters and the Destroyers lack of backup systems. I'd say the Death Star would chew the Borg a new one, though

And as for the who would win, Chewy or Data- I think you're comapring the wrong ones. It should be Chewy or Worf. If anything, Data should be compared to Vader, or Grievous in upcoming Episode 3.