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The man was riding on the road when he collided with the cars, Greater Manchester Police said.
The incident took place on New Year's Day on Springfield Road in Tameside at about 1.40pm.
Emergency services pronounced the man dead at the scene. No arrests have been made and enquiries are ongoing.
Sergeant Marie Eldred, of GMP's Serious Collision Investigation Unit, has appealed for witnesses.
"Our thoughts remain with the man's family as they come to terms with this incredibly tragic loss," she said.
"This collision happened in the middle of the day so we are hopeful that there are a number of witnesses who may have dashcam or CCTV footage."
Anyone with information should contact the Serious Collision Investigation Unit on 0161 856 4741, quoting incident number 2518 of 01/01/22. Reports can also be made anonymously to Crimestoppers on 0800 555 111.