High Quality Content by WIKIPEDIA articles! The Herts Senior Cup, officially titled the Hertfordshire County Football Association Senior Challenge Cup, is the oldest County-based football Cup competition based exclusively in Hertfordshire, England. It was first contested in the 1886-87 season and won by Hoddesdon Town. It has been contested every year since except for the years 1915 to 1918 when it was suspended during World War I. It is usually contested by the twenty-two most senior Clubs in the County, though this number has been higher and lower in previous years.