The oldest version of Windows is Windows 1.0, released in 1985. The oldest version of Windows that still receives security updates is Windows 2000.
Windows has launched its latest and most advanced version of Windows named Windows 7 on July 22, 2009 for testing and developers and on October 22, 2009 for Public.
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according to wikipedia,
LEO I 'Lyons Electronic Office' was the commercial development of EDSAC computing platform, supported by British firm J. Lyons and Co.
and it was founded in 1951, making it the oldest operating system.
Likely the first operating system was built for the IBM 360 computer mainframe. It came about during the 1960s and steadily became more complex.