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A 32-year-old local man was riding his bike along Thornaby Road at approximately 6.10pm on Monday 30 December.
At this time, four men dressed in black clothing and wearing balaclavas, came out of the bus stop and demanded that he give them his bike.
One of the men has then pulled out a zombie knife to use to threaten the victim.
The men then stole the bike and made off in the direction of Northumberland Road.
On the same day, at around 9.40pm, a 16-year-old boy was walking home from a local gym on Middlesbrough Road when he noticed two males on separate bikes who kept turning around to look at him.
As he crossed the road and made his way onto Acklam Road, the males approached and grabbed him. One of the males was armed with a knife which was used to threaten him.
The men began rummaging through his pockets before stealing an iPhone.
As part of detective’s enquiries, they are appealing for anyone who may have been in the area at the time or has information that could assist with the investigation, to get in touch.
Detective Inspector Carl Blenkinsop, from Stockton CID, said: “I am keen to hear from members of the public who were in the area at the time and may have seen these males acting suspiciously or may have information as to their identity.
“I also want to hear from anyone who saw the robberies take place and if you have any dash cam or mobile phone footage to please get in touch.”
Anyone who has information is asked to contact Cleveland Police on 101 or to visit the website. Please quote reference number 245172 for the robbery on Thornaby Road and reference number 245276 for the one on Acklam Road.
Information can also be provided anonymously by calling the charity Crimestoppers on 0800 555 111.