Who do you think would win a chess match? Data from Star Trek the Next Generation or Deep Blue? 

I didn't really follow star trek that much. Does it imply in any episode that Data has some phenomal chess program built into him?

Data of course!!1

Yes, I really don't think a 20th century computer could put up much of a fight against a 24th century positronic brain with a type R phase discriminating cognitive amplifier.

Sure, Data might have to brush up on his openings for a week or two, but c'mon.  He could do that on the holodeck with Kasparov. 

Data, hands down, one half of deep blue is taking bookings for american airlines while data plays that 3d chess thing tink about it