http://www.youtube.com/watch?v=krD4hdGvGHM&feature=youtu.be
I would have to say NEVER.
...
reasonably sure it would be a first...
fred shero faced habs in '76 final as HC of the flyers, and in '79 as HC of the rangers...but in both matchups he was opposed by bowman...
in 1932, person irvin coached toronto vs ny rangers coached by lester patrick...
in 1953, irvin coached habs vs boston coached by lynn patrick, lester's son..
close but no cohiba corona