Craig Wardle, of Owers Avenue, was sentenced to 30 months in prison after admitting breaking the man's jaw in a brawl. He also pleaded guilty to charges of malicious wounding and affray.

Two of his friends, Karl Beeson, 19, and a 17-year-old both of Langley Mill, escaped jail for their part in the assaults.

Guy Napthine, prosecuting, told Derby Crown Court 20-year-old Wardle was part of a gang who approached Gilbert Ryan outside a pizza parlour on Station Road, Langley Mill, on November 17, 2006.

When Mr Ryan refused a request for a cigarette, Mr Napthine said: "words were said," and Wardle hit Mr Ryan on the side of the head.

A bone in Wardle's hand protruded through the skin with the force of the punch.

The court also heard, while Mr Ryan was lying injured, Worrell, of Cromford Road, threw a beer bottle that smashed near his head.

On June 8 last year, the friends fought with a father and son in Langley Mill.

They each admitted affray after the incident which left the father, Luke Drury, with cuts to the mouth and ear and his son, Alex, with a bump on the head.

Later the same day, Wardle approached a man at Heanor Memorial Park and, after speaking to him, hit his victim and broke his jaw. A titanium plate had to be fitted during surgery.

Defending Wardle, Catherine McKeever said: "It has to be conceded his record is appalling. He is still immature and irresponsible. But he has been working and trying to put his life right."

Sentencing him, Judge Andrew Hamilton said: "You are a violent and dangerous young man."

The 17-year-old was given a two-year community and rehabilitation order, 140 hours of unpaid community work and told to pay £350 compensation.

Beeson, of Milnhay Road, was given an 18-month supervision order and told to pay £200 compensation. The youth and Beeson were also given a curfew.

A fourth man also appeared in court and admitted his part in the affray, but his sentencing was adjourned until after a trial he is facing on another matter is heard in August.