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The side struggled in the middle patches of the game, but came home hard to score the final two tries and win thanks to an Aaron Smith try with five minutes left.
Smith sparked the side when he came on and the Highlanders woke up near the end to come away the victor.
The Chiefs looked lively on attack but ran out of gas in the dying minutes.
They started poorly but came alive in the second quarter of the game and led 19-10 at the break.
The Chiefs answered with three tries in the first half and held the ball better, not opting for the kick - which the Highlanders did way too much of after their early endeavours.
The game was played in stinking hot weather in the first half, but it cooled down in the second as the sun went down.
Highlanders 30 (Pari Pari Parkinson, Shannon Frizell, Aaron Smith tries; Josh Ioane 3 con, 3 pen)
Chiefs 27 (Tyler Ardron, Angus Ta'avao, Etene Nanai-Seturo 2 tries, Brad Weber 2 con, Stephen Donald pen)