The Sussex Senior Cup was founded in 1882 and we know that South Saxons entered the inaugural competition, but their progress is unknown. Hastings & St Leonards Swifts entered both the senior and junior cups for the 1889-90, but their progress is also unknown. As football grew in Hastings throughout the 1890s some strong teams were soon put together, but local teams tended to under perform in county competitions.
Hastings & St Leonards FC became the first team to reach the final in 1897, losing 3-0 to Eastbourne Swifts at the County Ground in Hove. The side lost by the same scoreline to Eastbourne (now Eastbourne Town) in the final the following year. The club once again reached the final in 1903 but were thrashed 7-0 by Eastbourne. St Leonards reached the final the following year but lost to Worthing, who have won the competition a record twenty-one times.
It was not until 1912 the trophy was brought back to town after St Leonards Amateurs defeated East Grinstead 4-1 at the Goldstone. It was another thirty years until a local side would once again reach the final, which saw Hastings & St Leonards lost to Eastbourne once more at the Dripping Pan; the side were runners up once more two years later losing to Worthing at the same ground. However the club won the competition for the first time the following year in 1936, defeating Lewes 2-0 in the final played at the Saffrons and would win the competition again two years later.
Hastings would go on to lose on two more occasions to Worthing, before losing their status as the most senior side in the area following the formation of Hastings United. The professional club would go onto only reach the final twice, facing Horsham both times. The first meeting ended in defeat in 1976, before getting their revenge three years later at the Goldstone.
Hastings Town would go onto reach the final twice in the 1980s, losing both times to Steyning Town, before winning the competition in 1995 after defeating Crawley Town 1-0 at Woodside Road, Worthing. St Leonards were successful the following year beating Saltdean United 2-1 before Hastings won the competition once more in 1998, who defeated Burgess Hill Town 2-1 at the newly constructed Broadfield Stadium. Hastings went onto reach the final for two consecutive seasons, losing to Worthing and a very strong Brighton & Hove Albion side. No local side have since found success in this competition.
To view the full list of winners see the Sussex Senior Challenge Cup Wikipedia Article.