The Chiefs suffered back-to-back Super Rugby defeats to Australian opposition after going down 25-20 to the Waratahs at Allianz Stadium on Friday.
The Kiwi outfit's losing drought in Sydney continued as their hosts managed to hold on for a deserved victory, having outscored the defending champions three tries to two.
Super Rugby rookies Cam Crawford and Israel Folau crossed for the Waratahs in the first-half, while replacement hooker John Ulugia's touchdown in the 77th minute proved to be the match-winner.
The Chiefs were forced to play catch-up for the majority of the match and their uphill climb began when centre Adam Ashley-Cooper sliced in between Aaron Cruden and Brendon Leonard before putting Crawford in for his debut try.
Brendan McKibbin failed to add the conversion to his earlier penalty, but the Waratahs' 8-0 lead wasn't a true reflection of their domination of territory and possession thus far.
In fact, the Chiefs were hanging on the ropes and things went from bad to worse when first full-back Andrew Horrell was forced off with a broken ankle and then his replacement Gareth Anscombe missed two shots at goal.
Folau then struck for the 'Tahs when he collected a cross-field kick to score his team's second try two minutes from half-time. This time McKibbin found his target, and the hosts went to the half-time sheds 15-0 ahead.
It was the first time the Chiefs were held scoreless in the opening half this season.
But the reigning champions fought back in the second-half with momentum swinging in their favour after a reckless high tackle by Sitaleki Timani on Tim Nanai-Williams earned himself a ten-minute spell in the sin-bin.
The Chiefs were able to capitalise with their one-man advantage when playmaker Cruden breached the defence before offloading to Anscombe who was in support as he brushed off defenders to bring the visitors back into the match.
Anscombe's try seemed to spark the Chiefs attack and the points scoring machine went close to nabbing his second if not for a try-saving tackle by Folau.
It was third time lucky for the Chiefs when prop Ben Tameifuna crashed over to give his side their first lead in the match after Leonard and Fritz Lee were denied earlier thanks to some desperate Waratahs defence.
Anscombe's conversion gave his team a short-lived 20-18 lead, before Ulugia crossed for the winning try with less than two minutes remaining.
Tries: Crawford, Folau, Ulugia
Cons: McKibbin 2
Pens: McKibbin 2
Tries: Anscombe, Tameifuna
Cons: Anscombe 2
Pens: Anscombe 2
Waratahs: 15 Israel Folau, 14 Cam Crawford, 13 Adam Ashley-Cooper, 12 Rob Horne, 11 Drew Mitchell, 10 Bernard Foley, 9 Brendan McKibbin, 8 Wycliff Palu, 7 Michael Hooper, 6 Dave Dennis (c), 5 Kane Douglas, 4 Sitaleki Timani, 3 Sekope Kepu, 2 Tatafu Polota-Nau, 1 Benn Robinson.
Replacements: 16 John Ulugia, 17 Paddy Ryan, 18 Mitchell Chapman, 19 Will Skelton, 20 Pat McCutcheon, 21 Matt Lucas, 22 Ben Volavola, 23 Peter Betham.
Chiefs: 15 Andrew Horrell, 14 Lelia Masaga, 13 Charlie Ngatai, 12 Richard Kahui, 11 Asaeli Tikoirotuma, 10 Aaron Cruden, 9 Brendon Leonard, 8 Fritz Lee, 7 Sam Cane, 6 Liam Messam (c), 5 Brodie Retallick, 4 Michael Fitzgerald, 3 Ben Tameifuna, 2 Hika Elliot, 1 Pauliasi Manu.
Replacements: 16 Rhys Marshall, 17 Michael Kainga, 18 Nick Crosswell, 19 Tanerau Latimer, 20 August Pulu, 21 Gareth Anscombe, 22 Tim Nanai-Williams.
Referee: Craig Joubert (South Africa)