The campaign was another disappointment for the Saints, who finished 19th in the league with 13 wins, nine draws and 20 losses – three positions lower than the previous season and four points above the relegation zone.
Due to the uncertain international economic landscape, the club was unable to make many significant signings in the summer, with Welsh full-back Tom Emanuel their most expensive transfer.
Alongside the Second Division and the FA Cup, Southampton played just one friendly match at the beginning of the 1938–39 season, against local rivals Portsmouth as part of the celebrations for the Football League's 50th jubilee.
The highest attendance was 23,104 against recently relegated Manchester City on 12 November 1938; the lowest was 4,196 against Burnley in the final home fixture of the campaign on 29 April 1939.
[2] Other successful early signings included Harry Brophy from Arsenal, who scored in each of his first four games when played as a "makeshift centre-forward", before spending the rest of the season at half-back and full-back;[3] Reg Tomlinson from Grimsby Town, who took over the centre-forward position and finished as the club's second highest goalscorer for the season;[4] and Tom Emanuel from Swansea Town, who replaced the outgoing Charlie Sillett at left-back.
Wing-half Alf Day, inside-forward Jimmy Woolf and centre-forward Billy Dunn all left the club after arriving only a year earlier, having made a total of 38 appearances combined between them.
[6][7][8] Long-time squad members Charlie Sillett and Arthur Roberts, both of whom were approaching the latter years of their playing careers, also left in the summer – Sillett, who made just shy of 200 appearances for the Saints in all competitions, joined Guildford City in the Southern League;[9] while Arthur Roberts, who had played over 150 games for the club, moved to league rivals Swansea Town.
[11] Right-back Frank Perfect arrived from Tranmere Rovers in January 1939,[12] while Harry Osman – the previous season's top goalscorer – departed Southampton in March for Millwall, who paid £3,500 for the winger.
The result was four consecutive defeats – 1–2 at home to Tottenham Hotspur, 1–2 at Burnley, 2–5 at Bury and 0–3 at Coventry City – which left the Saints at the bottom of the league table.
[28] After the March departure of Harry Osman, who had scored nine of the club's league goals up to that point, the Saints began to struggle even more – they lost four of their seven fixtures in April, including 2–6 and 0–4 thrashings at the hands of Luton Town, a 0–3 defeat by eventual champions Blackburn Rovers, and a 2–0 loss at home to mid-table West Ham United.