If you timeline them all out, the first story is the Wing Commander Academy pilot, "Red and Blue". Remember that you don't even see the Tiger's Claw in that one--it just ends with Blair finding out he's been assigned there. Next is the Wing Commander movie, which is Blair's first mission off the Tiger's Claw (in March).
The rest all jumble together--Wing Commander I starts in April and runs through November and the other episodes of Wing Commander Academy take place at times in there... as do the two movie spinoff novels.