The 1900–01 season was the 16th since the foundation of Southampton F.C. and their seventh in league football, as members of the Southern League.
The club were unable to repeat their success in the FA Cup and were eliminated in the First Round, but compensated for this failure by claiming the Southern League title for the fourth time in five seasons.
Club finances
The run to the FA Cup Final in 1900 had generated a surplus of £31 but the club were still £1,000 in debt. In July 1900, the company made a call on its shares in an effort to raise cash. The response to the call was disappointing with many shareholders having their shares forfeited as a result of their failure to pay the balance due.
The financial situation worsened in 1900–01, with the gates dwindling following the doubling of the entrance fees the previous year from sixpence to a shilling, and the club generated a loss of £740.
Personnel
After the disappointing end to the previous season and the embarrassing failure in the FA Cup Final, there was a "drastic" clear-out of players. Both the players at the centre of the dispute surrounding the team selection for the final, Roddy McLeod and Jack Farrell were released, as were defenders Meechan, Durber and Petrie. Another significant departure was Alfred McMinn who resigned as a director; McMinn had made a major contribution to the club's success, particularly with his ability to spot a good player, leading the "Stoke Invasion" in the summer of 1895.
The new recruits included three players from Everton, full-backs George Molyneux and Bertram Sharp and centre-forward Wilf Toman as well as former Everton and England forward Edgar Chadwick, who would renew his partnership with Alf Milward which had been described as "the best in the league" during their time together at Everton. From local football, the club recruited two players who were to play a major role in the future of the club: Bert Lee would have two long periods with the club as a player before becoming a trainer from 1914 to 1935. Fred Harrison would remain at The Dell for seven years and become the club's main goalscorer, with 88 goals from 166 appearances.
In view of the club's financial difficulties, the board also decided to recruit top amateur players. The first to join the club was Leslie Gay, who had made three appearances as goalkeeper for England in 1893 and 1894, although Gay never played in a first-team match for Southampton. Another amateur goalkeeper, the South African Wilf Waller also joined the club on a part-time basis and played in the opening match of the season when Jack Robinson was suspended. In December, C. B. Fry (described as "arguably the greatest all-round sportsman of his generation") did play for the club, making his debut at right-back in the Boxing Day match against Tottenham Hotspur. In January, the club made an offer to another Corinthian player, G. O. Smith, who had been the England captain and was widely considered as the world's best player of the 19th Century. The approach was unsuccessful, with Smith responding that he "thought it impossible to assist our club in cup ties [but] wishing us every success."
League season
The Saints started their attempt to regain the Southern League trophy with a 4–3 win at Luton Town followed by a defeat at West Ham United and a goalless draw at Portsmouth. Portsmouth were top of the table having won their opening three matches and the local newspaper claimed that, while Southampton were "under a cloud", "the Portsmouth star is shining conspicuously in the footballing firmament". A crowd of between 10,000 and 12,000 saw the clubs play a "clinking ding-dong, robust game" which Portsmouth looked most likely to win.
After this stuttering start to the season, the Saints settled down with a run of 12 victories in the next 13 matches. The final three months of the season were more erratic with three defeats in the final two months of the season, but the Saints had done enough to hang on at the top of the table, to claim the Southern League title for the fourth time.
The second meeting with local rivals, Portsmouth, came on Easter Saturday, 6 April. With three matches left to play, Southampton led the table but Portsmouth had a game in hand and could still overhaul the Saints, although their away form was poor. With Portsmouth having several players out injured, Saints took the lead after ten minutes when Milward was fouled; Lee's "beautifully placed" free kick was "piloted" into the goal by Milward. Milward scored again late in the second half from Edgar Chadwick's pass.