The 27-year-old man was attacked on Meadowcroft Road, Normanby around 10.30pm last night.
The five men aged between 20 and 31, have been arrested on suspicion of murder and remain in police custody awaiting questioning while inquiries into the incident are ongoing.
Cleveland Police have said the attack on the man is believed to have been targeted.
Police are still in the area conducting inquiries and providing reassurance to residents, while scene of crime officers are also in attendance at the scene.
A red car believed to be relevant to the investigation also remains at the scene.
A local resident told the Gazette Live: "I was out at about 10.20pm bringing my washing in.
"I just heard voices on the street. But there wasn’t really a commotion.
“Next thing, we just saw the blue lights. It went up the road and back down again. That was after 11pm last night.”
Anyone with information is asked to speak to an officer or call Cleveland Police on 101 quoting Event 66570.
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