I posted a more detailed analysis looking at the two teams and roster turnover(
http://forum.calgarypuck.com/showthread.php?t=145556) but just looking at their records:
Chicago:
2006/07 - 13th in conference, missed playoffs
2007/08 (Kane/Toews rookie year) - 10th in conference, missed playoffs
2008/09 - 4th in conference, eliminated in 3rd round
2009/10 - Stanley Cup
Calgary:
2012/13 (lockout year) - 13th in conference, missed playoffs
2013/14 (Monahan rookie year) - 13th in conference, missed playoffs
2014/15 (Gaudreau rookie year) - 8th in conference, eliminated in 2nd round
2015/16 - ???