Sri Lanka duo Dhananjaya de Silva and Kamindu Mendis frustrated England's bowling attack to ensure the tourists finished day two of the final Test on 211-5.
England resumed on 221-3 after bad light limited Friday's play, with Ollie Pope having reached his seventh Test century shortly before stumps.
The hosts enjoyed a major reprieve early in the morning session, with Harry Brook inexplicably dropped on 12 by Asitha Fernando after skewing Milan Rathnayake's ball horribly.
Brook's luck soon ran out as Kamindu took a stunning catch off his drive, but Pope was more fortunate to survive an lbw review after appearing to have been trapped for 139 by Vishwa Fernando's delivery.
Pope made it to 154 before being caught in the deep by Dimuth Karunaratne, Sri Lanka's second wicket in three balls, as they went on to make light work of the England tail.
Olly Stone was the pick of England's bowlers, taking 2-28 after first running out Sri Lanka opener Dimuth Karunaratne, while Chris Woakes dismissed Kusal Mendis before debutant Josh Hull took his first Test wicket, ending Pathum Nissanka's brilliant knock of 64, with Woakes taking a fantastic catch at cover.
Yet Hull dropped a gilt-edged chance to send Dhananjaya packing, and the Sri Lanka captain took full advantage, moving onto 64, with Kamindu on 54 at the other end, by the time bad light stopped play with the tourists trailing by 114.
Data Debrief: Kamindu England's bogeyman
Kamindu's tally has come from just 70 deliveries, at a strike rate of 77.14. He has scored 70+ in two of his last three Test innings against England, and he is well on course to make that three from four.
England stuttered in the field after an excellent start to defending their lead, though the hosts should still be confident. After all, they are undefeated in their last eight Tests at home (W7 D1).
Complacency not an issue in England display, insists Stone
Olly Stone denied complacency played a part in England's performance on day two of their final Test against Sri Lanka at The Oval.
England were bowled out for 325 after 69 overs, as Dhananjaya de Silva and Kamindu Mendis helped the tourists reach 211-5 at stumps.
Stone was the pick of the hosts' bowling attack, taking the wickets of Angelo Mathews and Dinesh Chandimal while also running out Dimuth Karunaratne.
De Silva, however, was crucially dropped by debutant Josh Hull, as he ended the day on 64 runs from 106 deliveries alongside Mendis (54).
And while England handed Sri Lanka a potential route back into the final Test, Stone was confident that on another day, they could have been out of sight.
"I wouldn't say we were complacent. We've always said about taking the positive option, sometimes you can sit there and take a few blows," Stone said.
"If you put a few chances away it can come out differently. On another day it goes another way, and we get a few on the board."
As it had done on the first day, bad light was a constant threat, resulting in fast bowler Chris Woakes delivering four balls of off-spin.
England had started brightly with the ball in hand, working through Sri Lanka's top order before being stopped in their tracks by De Silva and Mendis.
But the bad light inside The Oval played its part, with the tourists able to chip away at their target after tea.
Stone acknowledged the difficulty of the conditions but had words of praise for Hull after taking his first wicket on his debut.
"It was too dark for our seamers but we tried to take the positive option. We thought we could take wickets with our spinners," Stone said.
"We feel we have the bowlers in any conditions but Sri Lanka played well.
"Hull has been brilliant. He hasn't looked nervous - he has been smiley, he has enjoyed it.
"I know he will be better for taking that wicket and hopefully he can take more in the morning.
"There is no greater job in the world. Going out there with a smile on our face, enjoying it.
"It doesn't feel like international cricket, you are nice and relaxed and out there with your mates."
Babardian Chemar Holder signed by Durham for backend of County season
West Indies pace bowler Chemar Holder has signed for Durham to bolster the side for their final three Championship games of the county season.
The 26-year-old will replace New Zealand's Neil Wagner, who damaged his shoulder against Nottinghamshire in August.
Holder played his sole Test in New Zealand in December 2020 and also appeared in a one-day international against Bangladesh the following month.
“With international call-ups and a number of injuries, it was extremely important to bring in an additional seamer, and we are pleased to have secured a bowler of Holder’s quality," said director of cricket Marcus North.
Holder, who had a spell with Warwickshire in 2021, has taken 89 wickets in 27 first-class matches at an average of 29.60, claiming five or more in an innings on five occasions.
"It feels very good to be a part of Durham and to be playing county cricket for a second time," the Barbadian said.
He will be available for Monday's game against Lancashire at the Riverside.
Australia ease to T20I series sweep of Scotland
Australia overcame a rough start to their innings to ease to a six-wicket victory over Scotland in the teams' third T20I on Saturday, clinching a series sweep at The Grange.
Having been inspired to comprehensive victories by some expert batting from Travis Head and Josh Inglis in the first two matches of the tour, the visitors found themselves dropped to 18-2 as they chased a target of 150.
Scotland had been led by Brandon McMullen's 56 runs off 39 balls as they achieved a respectable figure despite the best efforts of Cameron Green, who finished with figures of 3-35 for the tourists.
It was also McMullen whose terrific diving catch sent Jake Fraser-McGurk walking for a duck before Head (12) swept Brad Currie's fourth-over delivery straight to George Munsey to put Australia in a spot of bother.
However, Green replicated his bowling heroics with the bat, hitting an unbeaten 62 off 39 balls to ensure Scotland's joy was short-lived.
Even the wicket of captain Mitchell Marsh, who dragged on for 31 runs from Jack Jarvis' rasping delivery in the 10th over, could not halt the tourists' momentum, and they got over the line with 23 balls to spare for just one further loss.
Data Debrief: Green shows all-round credentials
Australia's third straight victory in Edinburgh was slightly more testing than their previous two as the top order faltered, but they could count on an exceptional all-round showing from Green.
Having taken three wickets in a T20I for the very first time, he proceeded to also register his best batting performance in the format, beating his previous best of 61 versus India in 2022.
Had Scotland succeeded in setting a more challenging target, Green might have had his eyes on an even more impressive total, having slammed five sixes and two fours.
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