Charles Shiells, who gave up well-paid work in telecommunications to study for National Nursing Examination Board qualifications, won pounds 500 compensation for the first job refusal and pounds 600 for the second.
The head of one nursery allegedly told JobCentre staff that she did not want a man for the post because of the growing number of child abuse cases.
Ann Douglas told Department of Employment officials: 'Look, we live in the real world and know that the realities are that a man of 50 is no use to me and, besides, I only have one toilet.'
In a later statement, Mrs Douglas, of Tuebrook Tots Nursery, Liverpool, said that she had refused to give Mr Shiells a job because of his age, not his gender. One man already worked at the nursery part-time, she said.
An industrial tribunal ordered Mrs Douglas to pay Mr Shiells pounds 600 compensation under the Sex Discrimination Act. The previous hearing referred to a job he was refused in the Broadgreen area of Liverpool.
Pauline Mathews, a lawyer for the Equal Opportunities Commission which championed Mr Shiells' second case, said the decisions showed that times had changed. 'It is no longer acceptable for childcare to be seen as a job for women only. This should be a clear sign to employers that stereotyped ideas of 'women's work' and 'men's work' could land them in court.'
Mr Shiells, who has a 19-year-old daughter and who was divorced seven years ago, grew up with six sisters in the Tuebrook area of Liverpool. He started his NNEB course in 1986 and passed his exams in 1990. He worked part-time in local authority nurseries, but says that he faced prejudice in the private sector.
The latest tribunal heard that when staff at the JobCentre telephoned Mrs Douglas to say that Mr Shiells was interested in the job, she started laughing and said that she would not accept a man because she did not have toilet facilities. She said she wanted a woman for the job.