John Michael Woodward, 40, from Wombourne, was sentenced for harassment without violence at Shrewsbury Magistrates Court.
Woodward admitted sending numerous text messages to his former girlfriend, who lives in Shrewsbury, after she ended their relationship earlier this year.
Prosecuting, Mrs Kate Price told the court the victim had been left 'terrified' by the experiences that took place between May 8 and May 25.
She said: "She blocked him on her mobile but he used different SIM cards and messages started to come through again.
"He admitted it does look stalkerish and it does go beyond reasonable behaviour.
"He could see she had a right to be concerned about this."
Mrs Price added that the victim was 'terrified of him' after his persistence in contacting her.
Defending, Miss Vanita Joshi said: "The majority of the text messages he sent were pleading with her to take him back, to give him one more chance."
The court heard that in February this year, the former girlfriend took the defendant back before the relationship once again broke down in March.
Miss Joshi said: "He thought this was no different from all the other times they had broken up and got back together.
"He was not thinking at the time that this was the end of their relationship."
Woodward, of Bratch Lane, had been served a harassment warning in April to leave the victim alone before he was later arrested on June 12.
Miss Joshi added: "He now does realise the consequences of his actions."
Woodward plead guilty at an earlier hearing on June 25, which had been adjourned for a pre-sentence report.
In a victim impact statement, the court heard that the former girlfriend had paid for CCTV and alarms since the harassment and her daughter was 'fearful' of Woodward.
Read to the court by Mrs Price, she said: "I just want him to stop contacting me so my daughter and I can feel safe again."
Woodward was given a restraining order not to contact the victim directly or indirectly by any means and ordered to pay £400 compensation to the victim.
He was told he would not be able to go within 200 metres of the road she lives on in Shrewsbury, or the Shrewsbury area on days that tied in with her work.
He was fined £560 reduced to £375 because of his early guilty plea. He was also ordered to pay £37 victim surcharge and prosecution costs of £85.