The 1899–1900 season was the 15th since the foundation of Southampton F.C. and their sixth in league football, as members of the Southern League.

They ended the season third in the Southern League, but reached the final of the FA Cup, thus becoming the first southern professional side to do so, and the first side from south of the midlands since 1883. In the final, they played badly as a result of divisions amongst the players and lost 4–0 to Bury.

Start of the season Having won the Southern League title in each of the three previous seasons, Southampton were now considered to be the best football team in England outside The Football League. The club had considered applying to join the league but decided that, because of their location on the south coast, the cost of travelling would be prohibitive. The popular boys' newspaper, Chums featured the club in their October 1899 edition:The Southampton club is the surprise packet of the football world. No team can boast of having fought their way to the front with such lightning-like rapidity as the champions of the South and, if the opinion of experienced judges are worth anything, the Southampton men have absolutely no superiors. It is true that they do not engage in first League duels, but the reason they do not do so is not that they consider they stand no chance of achieving premier honours, but that the departure would not pay them. There are no League clubs in the South, the consequence being that if Southampton were to enter for the competition, about half their time would be spent in travelling to the North and back — a proceeding that would soon land them high and dry in Bankruptcy Court.

With the club £1,000 in debt and in an attempt to ensure success on the pitch, the directors had recruited several top-class players on substantial wages. In order to meet these, the cost of entry to home matches was doubled from sixpence to a shilling. The opening Southern League match was attended by a meeting of "anti-bobs" in Milton Road; "after [their] grievances had been aired, the participants therein wended their way to other haunts than the football field". As a result, the attendance for the match against New Brompton was "disappointingly small" with "barely two thousand people present". Explaining the decision to double the price of admission, the secretary Mr. Arnfield told the Football EchoCandidly, I don't like it personally, but if we don't get enough 'tanners' we must have the 'bobs'. There is [an] alternative ... to an occasional shilling gate, and that is to reduce the wages of players, which means inferior men. After all the brilliant players we have had, Southampton people won't put up with a mediocre team. Why, our people would throw bricks at us.The Board are particularly anxious to retain a good team, but you must remember we have a big deficit and our summer wage bill is within £12 of our winter one, whilst for over four months we have not taken a penny.

Players

During the summer of 1899, several players left the club including forward Abe Hartley, who joined Woolwich Arsenal, and Jacky Robertson, who joined Rangers, shortly after becoming the first Southampton player to play for Scotland in April 1899.

Three forwards joined the club in the pre-season: Jack Farrell returned from Stoke, where he had spent the 1898–99 season having played for Southampton from 1895 to 1898, and Archie Turner was recruited from East & West Surrey League club St. Michael's, Camberley, but the major signing was former England international Alf Milward from Football League Second Division side New Brighton Tower.

The team mow consisted mainly of experienced former Football League players. Ten players appeared in all six F.A. Cup matches and twenty or more Southern League matches, with Alf Milward being ever-present and becoming the team's top goal-scorer. The team had three past or present England internationals (goalkeeper Jack Robinson and forwards Alf Milward and Harry Wood), while full-back Peter Meechan had previously played for Scotland. Archie Turner was the only regular player to have been born in Hampshire and was also the only player not to have previously played in The Football League, but he ended the season by achieving the then unique distinction of being called up for England in his first season in first-class football, and also becoming the first Hampshire-born player to represent England.

Goalkeeper Jack Robinson had previously played for Derby County and was the current England international 'keeper. The full-backs were Peter Durber and Peter Meechan who had previously played for Stoke and Everton respectively. Centre-half Arthur Chadwick had previously played for Burton Swifts and would end the season with two England caps. Either side of him were Scotsmen, Samuel Meston (another former Stoke player) and Bob Petrie, formerly with Sheffield Wednesday. The centre-forward position was contested by Jack Farrell and former West Bromwich Albion and Leicester Fosse player Roddy McLeod. Alongside Archie Turner on the right was Jimmy Yates, previously with Sheffield United and Ardwick, with the two former England internationals, Alf Milward and Harry Wood on the left.

Several of the players were on high wages with Wood on £5 a week and Robinson earning £5 10s with the total wages bill exceeding £60 per week, which with bonuses put the annual total to in excess of £4,000, a total believed to be exceeded by only five or six Football League clubs.

In an interview with the boys' paper Chums, the club's "popular secretary and manager, Mr. Arnfield" said:In the main, [the cause of our success is] our bold forward policy of engaging only tip-top players. No man is good enough for us who isn't good enough to take his place in any team in England. We shouldn't dream of engaging a player who wasn't worthy of inclusion in the Aston Villa eleven, for instance. This is our Standard.

League season For the 1899–1900 season, the Southern League had been expanded from the 13 clubs, which had ended the 1898–99 season to 17 by the admission of Bristol Rovers and Queens Park Rangers and the promotion of Cowes and Thames Ironworks. The newly formed Portsmouth club inherited the place vacated by the Royal Artillery. Of the 17 clubs, Cowes and Brighton United failed to complete the season, with their records being expunged.

The season started with a comfortable home 6–2 win over New Brompton but this was followed by a draw at Gravesend United and defeat at home to Swindon Town. After the 3–1 victory at Bristol City on 23 September, Roddy McLeod was dropped to be replaced by Archie Turner on the right-wing. This was the start of a run of twelve games with only one defeat and by mid-January, the Saints were at the top of the table. Amongst the victories were defeats of Chatham 9–0 on 20 December (with four goals from Turner) and of Gravesend 8–0 on 6 January.

The season was then interrupted by bad weather and by the time the league restarted in early March, Saints were without Jack Farrell who had been seriously injured in the F.A. Cup match against Newcastle United. He was replaced by Roddy McLeod but the FA Cup run distracted the team from the league, which resulted in a run of poor performances. The 2–0 defeat at Tottenham Hotspur on Good Friday 13 April finally extinguished any chance of retaining the title.

There then followed consecutive matches against newcomers, Portsmouth to decide who would come second to Tottenham. The match at The Dell on Saturday 14 April was attended by "barely 3,000" supporters with the home fans being more interested in the Cup Final the following Saturday. Despite the Saints' best efforts, they were thwarted by "Gunner" Matt Reilly in the Portsmouth goal, and Saints went down to goals from Sandy Brown and Dan Cunliffe. The return match at Fratton Park two days later, was attended by an Easter Monday crowd of 10,000 supporters who witnessed a "complete triumph" for Portsmouth with the two goals coming from Sandy Brown and Billy Smith.

Saints' performance against Portsmouth was described as "poor in the extreme" and "there was really no comparison between the two teams". The Portsmouth manager, Frank Brettell described Southampton as "stale" and predicted a "comfortable" victory for Bury in the FA Cup Final.

After the humiliating 4–0 defeat in the final, Saints played out the remaining three "dead" matches including victories at home to Bristol City and Millwall, in both of which McLeod (who had not been selected for the Cup Final) scored.

The league season ended with Southampton third in the table, nine points behind champions, Tottenham Hotspur.

League results Date OpponentsH / AResultF – AScorers2 September 1899New BromptonH6 – 2Milward (2), Yates (2), Farrell, Wood9 September 1899Gravesend UnitedA2 – 2 Farrell, Milward 16 September 1899Swindon TownH0 – 1 23 September 1899Bristol CityA3 – 1Milward (2), Farrell14 October 1899Millwall AthleticA2 – 0Milward, Turner21 October 1899Queens Park RangersH5 – 1Milward (2), Yates (2), Turner4 November 1899ReadingH0 – 2 11 November 1899Sheppey UnitedA2 – 0 Meston (2)25 November 1899BedminsterA2 – 0 Farrell, Milward 2 December 1899Bristol RoversH4 – 0Milward (2), Farrell, McLeod16 December 1899Thames IronworksH3 – 1 Milward (2), Turner20 December 1899ChathamH9 – 0Turner (4), Farrell, Milward, Petrie, Wood, Yates26 December 1899Tottenham HotspurH3 – 1Farrell (2), Milward30 December 1899New BromptonA2 – 1Farrell, Milward6 January 1900Gravesend UnitedH8 – 0Farrell (2), Milward (2), Cavendish, Chadwick, Meechan, Yates13 January 1900Swindon TownA1 – 2 Meston3 March 1900Chatham TownA0 – 1 10 March 1900ReadingA0 – 2 17 March 1900Sheppey UnitedH5 – 0Milward (2), Wood (2), Farrell31 March 1900BedminsterH3 – 2Milward (2), McLeod7 April 1900Bristol RoversA3 – 1 McLeod, Wood, Yates9 April 1900Thames IronworksA1 – 4McLeod13 April 1900Tottenham HotspurA0 – 2 14 April 1900PortsmouthH0 – 2 16 April 1900PortsmouthA0 – 2 23 April 1900Bristol CityH4 – 1Milward (2), McLeod, Wood25 April 1900Millwall AthleticH 2 – 1 McLeod, Yates28 April 1900 Queens Park RangersA0 – 1

Legend WinDrawLoss

Top of league table

FA Cup In the FA Cup, Saints were no longer required to qualify and entered at the first round proper, where they met Everton, who had finished in fourth place in the First Division in 1899. Everton were easily beaten in a "stunning" 3–0 victory with former Everton player Alf Milward scoring twice.

The next visitors to The Dell were Newcastle United who Southampton had defeated at the same stage two years earlier. The match was played on 10 February 1900 in wintery conditions. With the match goalless, Jack Farrell was forced to leave the pitch with a dislocated left collar-bone. Southampton played on with ten men until the 50th minute, when referee Arthur Kingscott abandoned the match because of a heavy snowstorm. The sides met again the following Saturday, with Roddy McLeod replacing the injured Farrell. McLeod "seized the opportunity" and scored twice in an easy 4–1 victory.

The third-round match was played a week later against another First Division side, West Bromwich Albion against whom McLeod scored again in a 2–1 victory.

With fellow Southern League team Millwall Athletic having defeated Football League champions Aston Villa in their Round 3 match, after the third of three "epic confrontations", the four semi-finalists were Millwall and Southampton from the Southern League and Bury and Nottingham Forest of the Football League First Division. The draw for the semi-final paired the Southern League and Football League sides, thus guaranteeing that a side from the Southern League would reach the FA Cup Final for the first time.