Bartolo Colon has a 3.00 ERA against the Red Sox this year, with a .222 BAA, and 1.20 WHIP. That's a lot better than Lackey has been against the Yankees. I'm also a little afraid that Colon may need "medical attention" in the DR again before the playoffs.
You also didn't mention Hamels. In all reality, Lackey will pitch against Fister/Scherzer, then Colon/Nova, then Hamels/Oswalt. Lackey fits as a #4 starter, but some of those #3s concern me, especially Hamels without a DH.