The cyclist, a 19-year-old man, was hit by a Vauxhall Corsa in Darlaston around an hour after the same is thought to have smashed into Boots in Wolverhampton city centre.
In total five people have been arrested over the incidents – including three people suspected of causing death by dangerous driving. All three were arrested in the Walsall area but away from the crash scene.
The ram raiders targeted Boots in Dudley Street late on Thursday evening and were spotted by officers on patrol at around 11.50pm.
A 22-year-old man was arrested at the scene on suspicion of burglary but other members of the gang escaped after a police car was rammed by the red Corsa as it fled Dudley Street.
Just over an hour later, a police car was in the Darlaston area when a car thought to be the same Corsa crashed into the cyclist on Midland Road.
Police officers carried out CPR on the teenager with the help of firefighters but he was pronounced dead at the scene, while the Corsa overturned and ended up on the side of the road.
A 33-year-old woman thought to have been a passenger in the Corsa was arrested at the scene on suspicion of burglary and taken to hospital.
Two other women, aged 21 and 39, and a 36-year-old man, were later arrested on suspicion of causing death by dangerous driving and burglary. All five suspects remained in custody on Friday evening.
Inspector Chris Fox said: “This is a really complicated investigation and we are still piecing together the circumstances leading to the tragic death of a young man.
“Although we have made several arrests, we are still urging anyone with information on both the ram raid and the collision to contact us.
“The road remains closed as we conduct forensic examinations, and we thank everyone for their patience.”
Midland Road, which runs under the Black Country Route between Willenhall and Darlaston, was cordoned off in the aftermath of the crash as detectives started their investigation.
Meanwhile Boots was open as normal on Friday but with one of its front windows boarded up.
West Midlands Police said the police car that was near the scene of the crash was not believed to have been chasing the Corsa but the force's professional standards department and the Independent Office for Police Conduct have been made aware.
A West Midlands Ambulance Service spokesman said: “Crews arrived to discover two patients, one of whom, the cyclist, was in a critical condition.
“Colleagues from the police were already administering CPR on our arrival and were assisted by colleagues from the fire service.
“Ambulance staff administered specialist trauma care and administered advanced life support but sadly, despite everyone’s best efforts, it became apparent nothing could be done to save him and he was confirmed dead at the scene.
“There was one patient from the car, a woman, who was a front-seat passenger.
"She was out of the car on our arrival and after receiving treatment for non life-threatening injuries, she was taken to Walsall Manor Hospital for further assessment.”
West Midlands Ambulance Service sent two ambulances, two paramedic officers and a MERIT trauma team to the scene, which included a doctor and a critical care paramedic. The first resource was on scene within three minutes.
Anyone with information or dash cam footage is urged to contact police via live chat on the website or by calling 101. Quote log number 106 of 27/11.