The club struggled at the beginning of the league campaign, remaining in the bottom half of the table due to a run of poor results.

The team remained in the top half of the Second Division table for most of the rest of the season, finishing in seventh place with 17 wins, 11 draws and 14 losses.

In May, inside-forward Tommy Taylor joined Welsh side Rhyl Athletic,[1] while centre-forward Douglas Vernon – signed as an emergency replacement for Willie Haines in February – was recalled by the Royal Air Force.

[4] Also in June, the Saints signed inside-forward Bill Fraser from Aldershot Town in an "unusually complicated deal" including an initial payment of £60, another £200 from a friendly match between the two sides, £50 if he made 20 appearances for the first team during the season (which he did not), and a 5% share of any future transfer fee.

[11] In March the club signed forward Thomas Groves from Blakenall and Scottish half-back Alex Sharp from Ayr United,[12][13] with Warren also returning on professional terms.

[14] During the game, Jerry Mackie became the first Southampton player to be sent off since James Moore in December 1920, as the Saints lost 3–1 and started off in the bottom half of the Second Division league table.

[15][16] A 2–2 draw with Hull City was followed by home wins over Blackpool and West Bromwich Albion,[17] which helped the Saints move up to seventh in the league.

[18] Dick Rowley quickly established himself as the season's top scorer with consecutive hat-tricks against Chelsea and Nottingham Forest in late September, the latter of which was a 5–0 away win,[17] and later became the first Southampton player to score four goals in an away match when they beat Bradford City 5–2 on 2 November.

[15] After Rowley was sold to Spurs in February, the club struggled to continue scoring and ultimately dropped too many points to remain in the fight for promotion.

Southampton entered the 1929–30 FA Cup in the third round against Second Division rivals Bradford City, who they had recently beaten 5–2 in the league.

The First Division visitors won the match 2–0 thanks to a pair of goals from centre-forward Methuen, although the Evening News admitted that Portsmouth were "somewhat lucky to win".

[17] Goalkeeper Willie White made the most appearances for the club during the campaign, missing only two league games and the FA Cup fixture.