Season 1904/05 was City’s first trophy year when they won the North Division championship.

Winchester then stayed in that division until 1928/29 when they were promoted to the county division after finishing runners up. In the first season City won the North Division as well as the Championship shield.

1929/30 saw City finish runners up to Newport, after this there were no more championships until the late Forties. City then held a mid table position until the middle fifties when relegation meant a drop into Division Two. This was short lived when the next season City were promoted as Champions to the top flight.

In season 1969/70 City won promotion back to the top flight this was followed by the clubs ambitious move into the new Southern League, the next year.

During the two seasons City found life hard and financial reasons resulted in the club dropping back into the Hampshire League. A drop through the leagues over the next few years was only broken when in 1991/92 the club won the division two championship.

1993/94 saw City win their first trophy for some time, when at Fareham Towns Cams Alders ground where they defeated Cowes Sports to win the Trophyman cup final. Season 1994/95 saw a new committee and a chairman elected to steer the club into the next century, with a matchday programme being printed and a souvenir shop opened and run by Terry Bone, within the clubhouse.

That season the Club held mid table position and at the end of the season the ground was enclosed with a fence to enable an admission charge to be taken at each home game.

1996/97 saw another manager take control and steer the club to the semi final of the Southampton Senior Cup only to lose to a strong Eastleigh side. The season was full of optimism and a mid table position was achieved.

In 1997/98 the Club went through a change with the chairman standing down and other members calling it a day, so it was left to a small hard working group to carry on.

1998/99 saw what was nearly City’s last season in football as the Club fought against financial problems, which nearly caused the committee to call it a day. Rescue packages were launched and out of that came the foundations, which saw the Club return to a firm financial standing.

1999/2000 saw Winchester City in the First Division and what a season they had. Good Cup runs and only a narrow defeat against Blackfield & Langley prevented Winchester from going to the Southampton Senior Cup Final at the Dell. The reserve side reached the Combination Cup final and who will forget the fantastic support that night at Alton with both teams also finishing in the top four of the league it was a very good season.

Season 2000/01 saw Mark Smith appointed as first team manager with Mark bringing in a lot of Wessex League experienced players. The prospect of Hampshire League Premier Division football was achieved on the penultimate game of the season against Fleet Spurs adding to the winning of the last ever Southampton Senior Cup Final to be played at the Dell.

The Club also won the first Inter League Shield, which they retained in season 2001/02. The reserves under Keith Curtis achieved second place behind Colden Common in the Combination Division One.

Season 2001/02 saw the merger of the two Winchester clubs, City and Castle, with the first and second teams playing at the City Ground and the North Hants League and Winchester League sides playing at Chilcombe.

With the installation of new floodlights and erection of a stand, the combination of a new chairman, Richard Newsome, and a business committee the club look forward to a new era with the goal of the Wessex League and beyond just around the corner. Mark Smith departed mid season to be replaced by Steve Whicher, who was joined by Bob Higgins and David Malone from Bashley and their Southern League professionalism. Unfortunately the first team just missed out on promotion after finishing third. However the reserves under the guidance of Paul Bodin won the Hampshire League Combination title along with the North Hants Senior Cup, Andover Open Cup and the Hampshire Intermediate Cup as well as being finalists in the Basingstoke Senior Cup. The side gained promotion to the Jewson Wessex League Combination. Lance Macklin is at the helm of the North Hants League side.

Season 2002/3 saw further changes at the first team helm, as the Club seeked to gain promotion to the Wessex League. A further change though to the manager’s chair early in January 2003 saw Neil Hards assume the role. Hards furthered the success of the season finishing as Trophyman Cup winners, Hampshire League Premier Division Champions and also Southampton Senior Cup winners as well as reaching the Quarter Finals of the F A Vase in their first season in the competition. Promotion to the Wessex League was attained.

The 2003/04 season surpassed all previous successes. Champions of the Wessex League and Winners of the Wessex League Cup, and then the FA Vase was won with a terrific 2-0 win over AFC Sudbury at St Andrews in Birmingham in front of a horde of travelling supporters who had made the trip up from Winchester.

Season 2004/05 again saw success for the team with a thrilling victory over Conference side Aldershot Town in the final of the Hampshire Senior Cup at Dean Court Bournemouth. The team also narrowly missed out on the championship and further promotion finishing 2nd in a finish that went down to the final day of the season.

Steve Tate, a member of the FA Vase winning team, took over from departing boss Steve Moss in October 2005 and assisted by Keith Williams, saw his side remain unbeaten for the rest of the league campaign to regain the championship title by 13 clear points and secure promotion to the southern League for the 2006/07 season