I debugged the film and everything was working as expected, it's just a lucky distribution of hits for the guy in the first plane.   You hit him with 9 .50s and 21 .30s.  No 37mm hit.  You smoked his engine and wounded the pilot and came within a sneeze of exploding him.  The second plane you hit with 2 .30s, 2 .50s and a 37mm.  The 37mm knocked off his tail.