After a goalless draw at The Dell, the sides played a replay at Clapton Stadium which the hosts won 2–1, eliminating the Saints at the first hurdle for the third time in four seasons.

The club's first signing in the summer was Portsmouth centre-forward Willie Haines, who joined from the First Division side having scored 119 goals in 164 league appearances.

[2] In June, outside-right Cuthbert Coundon was sold to Wolverhampton Wanderers for £150,[3] and inside-left Sam Taylor joined Halifax Town in the Third Division North.

[5] In August, the club signed outside-right Bert Jepson from Huddersfield Town,[6] as well as trialist Tom Sloan from Craghead United (he left a month later).

In September the club signed outside-left Johnny Arnold from Oxford City,[8] and in October they brought in inside-left Herbert Coates from the Royal Navy.

[11] Due to ongoing injury problems for his side's regular centre-forward Haines, in February 1929 Chadwick brought in former Royal Air Force aircraftsman Douglas Vernon to help with the end of season run-in.

[12] The final signings of the season were goalkeeper Bert Scriven from Totton and inside-left Ernie Warren from Third Division North side Lincoln City in March 1929.

[18][19] The run included a 2–1 defeat of recently relegated side Middlesbrough, home and away wins over Port Vale, and a 4–0 besting of Preston North End, who had finished just four points shy of promotion to the First Division the previous season.

[23] However, the team began struggling for goals due to Haines being injured, with his replacement Douglas Vernon failing to score in his five league appearances.

[12] A string of three consecutive losses in March saw the team as low as seventh in the table, although wins over Nottingham Forest and Millwall at the tail end of the month brought them back into the top four.

[14] The replay at Clapton Stadium started well for the Saints, who went ahead through Arthur Bradford and almost doubled their lead courtesy of Stan Cribb.

However, the hosts equalised before the end of the first half and continued to pressurise the visitors throughout the second, eventually scoring a second past deputising goalkeeper George Thompson.

The first was a friendly match against Southern League side Guildford City on 17 April, which ended in a 2–1 win to the visiting Saints thanks to goals from Willie Haines and Johnny Arnold.