Season 1890-91

Town entered the FA Cup for the very first time with a large crowd witnessing a 2-0 win against Reading at Portman Road (George Sherrington and Stanley Turner the goal scorers). Further victories against Norwich Thorpe and Huntingdon County followed before a 4-1 home reverse to the 93rd Highlanders stopped Town from reaching the first round proper at the very first attempt.

Season 1891-92

The penalty-kick is ‘invented’ with Fred Turner converting Town’s first ever spot-kick in a 7-0 win against Saxmundham. Hopes of a repeat of the previous seasons FA Cup exploits are short lived with a 5-0 defeat at the hands of Old Westminsters in the 1st Qualifying Round. A Canadian/American Touring side become the first foreign side to play at Portman Road and lose 2-1, and three Town players are in the Suffolk County side that take on and lose to Preston North End, the first professional side to visit Portman Road.

Season 1892-93

Royal Arsenal, shortly to be elected to the Football League, and considered to be the strongest club in the south of England defeat Town 5-0 in a friendly at Portman Road, despite having inside left Elliott sent-off. Ernest Aldous Kent hits five hat-tricks during the course of the season and Town score after just 5 seconds in a 5-0 win over Sudbury Town.

Season 1893-94

Town enter the FA Amateur Cup for the very first time. 123 goals are scored in 29 matches over the course of the season with Town victorious in 22 of them including a 13-0 drubbing of the 58th Regiment Northants.

Season 1894-95

The 1894/95 campaign proved to be one of the most exciting of the clubs amateur years. Victories against Norwich CEYMS, Peterborough Town and the 2nd Scots Guards propelled Town into the last 16 of the FA Amateur Cup where they lost 7-3 in a replay to the Old Etonians, twice winners of the FA Cup, after a 1-1 draw at Portman Road. A 1-0 defeat at the hands of Saxmundham stopped Town from reaching the Suffolk Senior Cup final but as the season drew to a close it was off-fields events that took the headlines as Town declined an invitation to join the newly formed Southern League and any immediate possibility of turning ‘professional’.

Season 1895-96

Town won the Suffolk Senior Cup and also undertook there longest away journey to date when they travelled to the North East for an FA Amateur Cup 2nd Round tie against Bishop Auckland. A crowd of 2,000 saw the home side win by three goals to one.

Season 1896-97

Sparta Rotterdam became the first continental side to play at Portman Road were they were defeated 10-0 by an Ipswich representative XI and Town won the Ipswich Charity Cup beating Beccles Caxton after a replay.

Season 1897-98

Town again decline an invitation to take part in league football – this time from the Norfolk & Suffolk League. Of Town’s friendly fixtures fourteen were against London opposition, all of which were played at Portman Road, while Tom Haward became the first Town player to be sent-off when he was dismissed in the game at Framlingham College. The Ipswich Charity Cup was retained and Aston Villa, Football League and FA Cup double winners the previous season, attracted a crowd of 5,000 when they visited Portman Road to take on Suffolk County.

Season 1898-99

With a no league football, and no Grandstand at the ground, the Club are described as ‘fossilised amateurs’. The Ipswich Charity Cup is won for the third year in succession but Town lose heavily to Beccles Caxton in the semi-final of the Suffolk Senior Cup in an otherwise unremarkable season.

Season 1899-00

League football arrives at Portman Road as Town finish a creditable fourth in the Norfolk & Suffolk League with the clubs first ever league match ending in a 1-1 draw with Norwich CEYMS. Two men of the cloth, the Revd M.W. Murray and Revd H.A.P. Gardiner, were frequent members of a side that won the Suffolk Senior Cup for the first time in four years with a 3-1 final win against Sudbury and retained the Ipswich Charity Cup for the fourth consecutive year. Complaints by the Ipswich & East Suffolk CC about damage to their crease results in the relocation of the football pitch at Portman Road to its present day location (it was previously aligned from East to West on the area now covered by the practice pitch).