The 1898–99 season was the 14th since the foundation of Southampton F.C. and their fifth in league football, as members of the Southern League.
They ended the season as champions of the Southern League for the third consecutive season and reached the Third Round of the FA Cup where they were eliminated by Derby County of the Football League First Division.
Pre-season
Having spent two seasons as temporary residents of Hampshire County Cricket Club, the "Saints" became resident at a new stadium about 200 yards down Northlands Road, nicknamed "The Dell", which had been built by George Thomas, a fish merchant who was a director of the football club. At the time of its opening, The Dell was considered to be the most compact ground in the country — the players got their first taste of their new home when they participated in a sports meeting there on 27 August 1898.
Determined to build on their success of the previous season, the club signed several new players during the summer of 1898, including five present or former internationals — Scotsmen Geordie Dewar, Peter Meechan and John Robertson and Englishmen Jack Robinson and Harry Wood. Robinson, the current England goalkeeper, and Robertson had played against each other in the Scotland vs. England international at Celtic Park on 2 April 1898, in which England were 3–1 victors, thus claiming the 1898 British Home Championship.
League season
The first league season in the new ground started on 3 September 1898, with a match against Brighton United, who were playing their first-ever league match. On a hot Saturday afternoon, in front of a crowd of 6,524, the Mayor of Southampton (Alderman G.J. Tilling) kicked off "like an international". The Saints soon took the lead when with "a little finessing", Tom Smith passed the ball through to Watty Keay who scored The Dell's first goal. Jim McKenzie missed some good chances and, with Southampton attacking in numbers, Bullimer in the Brighton goal was kept busy. Towards the end of the first-half, Arthur Chadwick accidentally caught Brighton's centre-forward Willie McArthur on the chin with a high kick. Bleeding profusely, McArthur left the pitch and Brighton had to continue with only ten men. Shortly before the interval, Abe Hartley scored the second goal, after a smart run up the left by McKenzie. In the second half, McKenzie added a third before Roddy McLeod reduced the deficit. With over a quarter of an hour to play, Smith completed the scoring, with a goal described as "just such a goal as there is no doubt about – a shot which beats the goalkeeper almost before it is made".
Despite having signed five present or former international players during the summer, Southampton were unable to dominate the league as they had done in the previous year, losing their second match to New Brompton and drawing four matches before the New Year. In November, the referee, Mr. T.W.H. Saywell, mistakenly ended the match at Millwall ten minutes early with Southampton leading 4–1. He soon realised his error and tried to bring the teams back to complete the match, but the crowd had invaded the pitch and refused to leave. The match was completed five months later on 12 April 1899 before a Western League match at The Dell, with no further score.
On 3 December, the Saints defeated Warmley 6–0 at The Dell, but this result was expunged when Warmley withdrew from the league before the end of the season. Reserve goalkeeper, John Joyce made his "debut" in this match, but with the result being expunged, had to wait until 21 October 1899 before his official debut. The New Year started with two away defeats; in the match at Sheppey United on 7 January, Arthur Chadwick was dismissed, becoming the first Southampton player to be sent off in a league match.
The Saints won five of the next seven games and entered the last day of the season level on points with Bristol City, their final-day opponents. Bristol City were playing their second season in the Southern League having finished as runners-up in 1897–98, and were undefeated at their St John's Lane ground. Southampton had the superior goal average, so a draw would give them the title for the third time.