A car has been filmed driving the wrong way down the A66 in a similar stunt to the fatal crash in August which killed seven people.
Two 16-year-old boys were inside the Renault Megane which fled police just after midnight last Wednesday.
The car hit street furniture before driving the wrong way down the A66, where a West Yorkshire Police officer arrested both boys.
It comes just two months after seven people, including two police officers, were killed on the road in Teesside when a Volkswagen Passat hit an oncoming Cleveland Police car while trying to evade other officers.
PC Matthew Blades, 37, and PC Tom Clough, 38, died at the scene after the crash, which took place around 3.39am on August 22.
Five men in the VW – Michael Robert Cahill, 23, Jakub Matusiak, 23, Makai Saddington, 18, and 17-year-olds Theo Rae and Cole Robert Worthy – also died.
There have now been 50 arrests as part of a wider police operation against organised crime following the crash.
After the boys inside the Renault were arrested last week, one pleaded guilty to dangerous driving and disqualified driving at Teesside Magistrates' Court.
Police chased a Renault Megane on the A66, one of three occasions within a week where cars drove the wrong way down major roads in similar stunts to a crash in August which killed seven
Two 16-year-old boys inside the car were arrested, with one pleading guilty to dangerous driving and disqualified driving
He will be sentenced in November.
The second boy was arrested on suspicion of possession with intent to supply class A drugs and was bailed while a police investigation continued.
It was one of three occasions within a week where cars drove the wrong way on major A-roads near the scene of the fatal crash in August.
In a second case, a car drove away from officers on Cambridge Road in Middlesbrough around midnight on October 12 before turning on to Acklam Road and then driving the wrong way down the A66 towards the town.
Cleveland Police said an investigation into the driver of the car was ongoing.
And three days later police were called to a report of a Volkswagen Passat driving erratically in Thornaby around 1am.
The car then drove dangerously and against the flow of traffic on the A19.
Chief Superintendent Paul Richardson said: 'We have seen a number of incidents in the last week, including where two young people have risked their lives, and the lives of other innocent road users, by driving dangerously. Staggeringly, this has included some driving contraflow on our busiest roads in Cleveland.
'This puts people at immediate, serious risk of harm or even death.
'It is truly shocking to see drivers take these risks, and we want those people to know that we will come down hard on anyone who thinks this behaviour is acceptable, and we will use the full force of the law in identifying, investigating and prosecuting anyone who commits these offences.
'We do not want to see anyone else harmed as a result of this behaviour, and so I ask those people to please think twice before committing these extremely dangerous acts.'
PC Matthew Blades and PC Tom Clough were killed when their police car was struck head-on by a Volkswagen Passat travelling the wrong way down the A66 near Middlesbrough
Their car was hit by the VW as it drove the wrong way along the dual carriageway in Teesside
Makai Saddington, one of the five killed in the Volkswagen, posted videos on TikTok of him being chased by police and was awaiting trial for racially abusing and assaulting officers
Close friends Theo Rae (left) and Cole Worthy also died in the crash in August
Michael Robert Cahill and Jakub Matusiak also died in the VW Passat
Cleveland Police, one of the smallest forces in Britain, saw its resources stretched to breaking point in the aftermath of the August crash as authorities feared a descent into gang war.
Violence spiralled across Teesside and was believed to be a reaction to the A66 crash.
The area's MP Andy McDonald said his constituents were 'not feeling safe' to go shopping while former Middlesbrough mayor Andy Preston said the town was 'on its knees'.
Hundreds of police officers were drafted in to restore order in Middlesbrough, which has the highest crime rate in England, excluding central London.
Mr Preston described Middlesbrough as England's crime capital where criminals can do 'what they want' and dominate the streets.
He warned that ordinary people were facing death threats, seeing guns shot at front doors and cars rammed into houses.