Jose Calderon had a lot of success against Derrick Rose in Rose's first two seasons in the NBA because he was far smarter and a more effective PG in the NBA. Rose was a strong scorer (albeit with mediocre efficiency) who was still learning how to run a team and gave inconsistent (usually lack of) effort on the defensive end of the floor.
Since Thibodeau came in and since D-Rose took his game to another level, it has been one way traffic in Rose's favour. Just like it was always going to be in the end. D-Rose just needed time to learn his trade. Calderon took advantage of the youngster as he does with most young PGs.
It is a good example of how underrated Calderon is as a PG + how overrated score first PGs (Lillard, K.Irving) can be in their first years before they learn how to properly run a team and play quality defense.
Edit: Plus, Toronto had Chris Bosh kicking Joakim Noah's butt for those first two years too. Bosh had some really great performances against Chicago. Fun games.