Australia's pace attack took two late wickets with the new ball to reduce England to 233-5 at stumps and wrest control of the first day of the fifth Ashes Test.
After winning the toss and batting, England slipped to 95-3 before skipper Joe Root and Dawid Malan shared a 133-run partnership that frustrated the Australian bowlers for most of the evening session.
But with the sun setting and the new ball in hand, Mitchell Starc had Root was caught by Mitch Marsh at square leg for 83 in the penultimate over and then Josh Hazelwood had new batsman Jonny Bairstow caught behind with the last ball of the day.
Root, in particular, appeared disconsolate as he left the field after batting for four-and-half-hours and in sight of his first century of the series, after scoring three 50s in the first four Tests.
Malan was not out 55 at stumps and will need to stay at the crease with the lower order to give England any hope of salvaging one win in the series after surrendering the Ashes with losses in the first three Tests.
Australia's quick bowlers made early inroads into top order with Pat Cummins claiming the first two wickets, having Mark Stoneman (24) and James Vince (25) caught behind.
Alastair Cook, who scored an unbeaten 244 in the drawn fourth Test in Melbourne last week, continued his good form in Sydney, reaching 39 before being trapped lbw by Hazlewood, just five runs short of being only the sixth player to tally 12,000 Test runs.
Hazlewood pinned the veteran opener on his front pad and had the initial not-out decision overturned by the TV umpire on review to leave England at 95-3 and the majority of the near 45,000 Sydney Cricket Ground crowd delighted.
Only Sachin Tendulkar (15,921 runs), Ricky Ponting (13,378), Jacques Kallis (13,289), Rahul Dravid (13,288) and Kumar Sangakkara (12,400) have more Test runs than the 33-year-old English batsman, who will likely get another opportunity to reach the milestone in the second innings.