The ground has stood in the centre of the town of Boston since the 19th century, and has been given a variety of names since its construction.

For 40 years before York Street's current tenants, Boston United were founded it was known as 'Main Ridge'.

The new floodlights, erected in each of the four corners of the ground, allowed the Pilgrims to play in various floodlit competitions.

In 1977 York Street failed an inspection for league grading, leading to local fundraising in 1978 which resulted in new terracing, stands, floodlights, toilets, turnstiles and snack bars.

announced that the ground had been renamed to 'The Jakemans Stadium', following a sponsorship deal with Sutterton-based Jakemans Confectioners[1] In August 2021, it was announced that Railway Athletic FC of the Boston & District League would begin playing matches at York Street.

For this, the club had to install temporary seats in the centre of the Benton Brothers York Street End during their spell in the Football League, according to former Chairman Jon Sotnick.

The land could not developed before the lease ends, unless Boston United no longer existed or had found an alternative home.

Public meetings have been held inside the ground, as have Community Days and fireworks displays.

Independent (unaffiliated to a governing body) greyhound racing took place around the pitch at Shodfriars Lane from 1932 until 1939.

[3] Boston is the nearest railway station to the ground; it is less than 1 mile (1.6 km) away and sign posted throughout the town.