Perhaps "Captain" Carter will be taking a holiday among the Grampians this summer and coming back with a burly Highlander or two to help them to win the senior cup next year.

[4] Following the retirement of his brother Charles following injury, Frank Bromley took over permanently as centre-forward with former Southampton Harriers player Bob Kiddle alongside him.

Arthur Fry retired during the season, leaving goalkeeper Ralph Ruffell as the only remaining player from the side who played in the inaugural match on 21 November 1885.

[2] Writing some years later, F. J. Montgomery, who was a prominent committee member who also served as "umpire",[5] claimed that the players "baulked at the expense of new shirts" and as a result he paid for them personally.

This gave them a repeat of the previous season's semi-final against Cowes, who were defeated in a straightforward 2–1 victory in a match played in a gale-force wind.

[4] The semi-final, against Winchester Rovers was played at the County Ground in a snowstorm and match reports indicated that St. Mary's were "fortunate" to emerge with a 1–0 victory.

Altogether, over 2,000 paid for admission, which with ladies, members of the County Club, Bannister School, boysand officials, would give an attendance of something like 2,800".

This led to criticism in the Bournemouth Guardian that "with forwards equal to the defence, St. Mary's might play a good game with better clubs than we often see in Hampshire; though I still have my doubts about Aston Villa".

The penultimate match of the season was against the Aldershot-based Royal Engineers who had recently won the Hampshire Senior Cup for the second successive year.