With tough competition at the higher end of the Second Division, Southampton continued to drop points in key matches and finished the season in fifth place with 17 wins, 14 draws and 11 losses.

In the 1923–24 FA Cup, Southampton beat top-flight side Chelsea in the first round, followed by a home win over Second Division rivals Blackpool in the second.

The highest attendance was approximately 20,000 against Manchester United in the second home game of the season on 3 September 1923; the lowest was around 7,000 for the 6–0 win over Barnsley on 19 January 1924, and for the 5–0 defeat of Clapton Orient on 5 April 1924.

One of the first departures during the summer was inside-forward John Cooper, who returned to his former club Darlaston after having made just five league appearances with the Saints during two seasons.

[1] Also leaving was outside-left Joe Clark, who was sold to Third Division North side Rochdale after losing his place in the first team to Len Andrews late the previous season.

[2] Two players were brought in to take Clark's place – Elias MacDonald from Burton All Saints in May,[3] and Jimmy Carr from Reading in June.

[4] Also arriving in the summer were George Harkus, a half-back who joined from First Division side Aston Villa for £250,[5] and Harold Pearson, a forward who was transferred from Brierley Hill Alliance in the Birmingham & District League.

[9] The club signed another amateur player in November, bringing in outside-forward Stan Cribb from local side Gosport Athletic, although he would not turn professional until the following season.

[10] The same month, winger Bill Henderson was signed for a fee of £500 from Luton Town after Sammy Meston – one of the club's two regular outside-rights – broke his leg during a match against Bristol City on 6 October.

[13] The next month, Henry Johnson also left The Dell to join top-flight side Queens Park Rangers, after scoring three goals in eleven appearances during the season so far.

[16] The team's form quickly improved, however, as they beat Bury in the return fixture 3–0 and went on a seven-game unbeaten run to move up to the top five in the league table.

[16] Despite taking three points each from the games against Stockport County and Crystal Palace, the Saints were unable to move above seventh place in the table, as the sides above them continued to pick up wins.

[20] Southampton played much of the game with ten players, after left-back Fred Titmuss suffered a "freak injury" in which a blood vessel in his eyeball was burst by a loose shoelace, and was forced to be taken off amid fear of permanent eye damage.

[20] The hosts opened the scoring shortly after half-time courtesy of Harry Chambers, but the ten men of Southampton prevented conceding more until six minutes from the end, when Dick Forshaw doubled his side's lead and secured the result.

[24] The visitors took an advantage, as Stephen Dearn and Willie Haines put Pompey 2–1 up, with Bill Rawlings scoring in between the goals for the hosts.