Vincent Start committed a range of offences from driving without insurance to failing to pay the bill for a meal at a restaurant.
Mr Start teaches at the City of Portsmouth boys' school and became a teacher in 1999 after his business in Portsmouth failed and he went bankrupt.
England's General Teaching Council heard last week that at times of stress Mr Start had a tendency to behave in a dishonest manner.
He was arrested and given a police caution after failing to pay for the school staff Christmas meal in a Chinese restaurant in Portsmouth in December 2004.
Mr Start had put down a pound;150 deposit, but left before paying the Pounds 212 bill. He said he had been so drunk that he had forgotten and went back the next day to apologise and pay.
"At no time did I intend not to pay the bill," he told the disciplinary hearing in Birmingham. "I was stupid, I drank too much and I wandered off.
"I did not intend to steal from my colleagues. I was ashamed then and I am ashamed now."
In December 2003 he was given a conditional discharge for 18 months by South East Hampshire magistrates after dishonestly obtaining property.
He was charged after signing for 10 digital fireproof safes from a mail order catalogue which were not under his name. The safes were ordered by his son and Mr Start claimed he did not want his son to get in trouble and kept the safes in the garage untouched.
Mr Start was banned for three months and given 60 hours' community service after being convicted in March 2003 of driving without a licence and insurance.
The disciplinary hearing was told that he had also been in trouble for three incidents dating back to 1986 which included theft and deception. In April 1999, Mr Start was banned from becoming a company director for five years and given 125 hours' community service .
He told last week's disciplinary hearing: "I would like to go back in time.
I sit here remorseful and full of regret. I am ashamed of what I have done.
I have owned up and taken responsibility for my actions. I have learnt my lessons and I am able to move on."
Mr Start was supported by Michael Smith, head of City of Portsmouth Boys'
school, who described him as an outstanding teacher and a good role model for boys at his school.
Mr Smith said: "He has been punished for the things he has done and this has not affected the ability of his teaching."
Three offences were committed while he was a teacher and three before he qualified.
Terry Bladen, who chaired the disciplinary hearing, said he believed the allegations made against Mr Start were not relevant to his ability to teach.
"None of Mr Start's conduct had an adverse effect on his pupils and he has proven to be a teacher admired by all his pupils."