If I have an YT-1300 with Chewbacca as my pilot and R2-D2 as one of my crew members, would Chewbacca’s ability still cancel the face up damage card from R2-D2 adding a shield and rolling a hit?

Sorry if this has been asked already.

no. the face up card for chewbacca only occurs when dealt. if it gets turned up after it is already on the ship, chewie has no effect

Copy, thank you.

If I have an YT-1300 with Chewbacca as my pilot and R2-D2 as one of my crew members, would Chewbacca’s ability still cancel the face up damage card from R2-D2 adding a shield and rolling a hit?

Sorry if this has been asked already.

While your intent may be understood your question is not entirely clear. I have a little trouble with the term "rolling a hit" although you roll an attack die and use that result to determine if a damage card will get flipped or not. Remember that some consider a [crit] result the same as "rolling a hit" although it is not.

Chewbacca's ability, and the Determination upgrade as well, both look at incoming cards that are being dealt face-up. Cards that land on the ship have slipped past the defense and may not be manipulated without worrying about hitting the defense when they do.