The Bears had the upper hand early, going out to a 12-0 lead, after tries to Kyle Turner after just eight minutes, before Apisai Koroisau added his own four pointer in the 17th minute. Koroisau added the extras, signalling what could have been the beginning of a long night for the Wolves.
But the Bears failed to go on with the job after Koroisaus try, with the Bears going into the sheds leading with no change to the scoreboard.
The Wolves were a different side in the second half, making their intentions clear in the 44th minute with an unconverted try. But the Bears would score two more before the night was over with tries to Bennett Leslie and Curtis Johnston.
Norths performance wasnt enough though, as the Wolves continued a second half romp that saw Windsor take the two competition points with a 28-24 win.
The North Sydney Bears are still yet to play their round 16 NSW Cup match against the Illawarra Cutters, placing them in provisional fourth position ahead of this Sundays round 17 match against the Wyong Roos at Morry Breen Oval.
Windsor Wolves 28 (Vaipuna Tia Kilifi, Bryce Cartwright, Eto Nabuli, Geoff Daniela, Liam Ayoub; Wes Naiqama 3, Luke Capewell)
North Sydney Bears 24 (Apisai Koroisau, Kyle Turner, Curtis Johnston, Bennett Leslie; Apisai Koroisau 4)