Accused of not taking enough risks throughout the World Cup campaign, Osieck took a doozy with 13 minutes left.
Taking off Tim Cahill - whose international career has been built on the vital goal - for Kennedy was certainly the most extreme move Osieck has made in the 21-month qualification bid.
In pulling off a superstar, he pulled off a masterstroke.
Kennedy rose unchallenged to head home a goal which provided the much-needed circuit-breaker for a Socceroos team which was lacking the killer touch in front of goal for most of the match.
Not helped by a pitch uneven in surface and soaked pre-match and during by persistent rain, the Socceroos' feet so often stuck where they shouldn't, their passes went a yard further than intended, and their work in the front-third was untidy.
While the first 15 minutes suggested the Socceroos were switched on and sharp, Iraq's stoic defence and the occasional feigned injury blunted and frustrated the home side.
Brett Holman couldn't get warm, and it was his withdrawal for 20-year-old Tom Rogic on the hour - another brave move by Osieck - which gave the Socceroos the semblance of a spark.
He had three shots at goal in three minutes to bring the game to life as the rain teemed down.
Then, more frustration.
Robbie Kruse's 65th minute volley was ruled out because of an earlier foul by Sasa Ognenovski.
But it is dangerous to rule out a team which so often thrives with backs-to-the-wall.
Kennedy's goal sparked a human pile-up at the corner flag which gave the night its John Aloisi 2005 shirt-off, running down the sideline moment.
Osieck can take a bow.
So too can the Socceroos. Brazil beckons.
- AAP