After securing their Premier League survival on the final day of the previous season, the Saints fared slightly better in 1999–2000 as the club finished 15th in the table, eight points above the relegation zone.

1999–2000 was Southampton's last season to feature Dave Jones as manager – he was suspended in January 2000 whilst facing charges of child abuse in a previous job, with Glenn Hoddle taking his place temporarily.

After barely retaining their top-flight status the year before, Southampton made two key signings in the summer of 1999, bringing in centre-back Dean Richards and midfielder Trond Egil Soltvedt.

The highest attendance was 15,257 against West Ham United in February (Hoddle's first game in charge) and the lowest was 10,960 against Manchester City in the League Cup in September.

Having spent much of the previous season on loan at the club, in the summer of 1999 striker Steve Basham left Southampton to join Preston North End in the Second Division for a fee of £200,000.

[6][7] Ken Monkou left on the same day to join second-flight side Huddersfield Town on a free transfer,[8] while Portuguese winger Luís Boa Morte arrived from Arsenal for a fee of £500,000 a week later.

[17] December saw the £50,000 sale of Scott Hiley to local rivals Portsmouth,[18] as well as the cancellation of a season-long loan deal for Portuguese centre-back Marco Almeida, who had made just one substitute appearance for the club since arriving in July.

[20] The next month, following extended negotiations to secure a work permit, Latvian winger Imants Bleidelis joined from Skonto – the same club from which the Saints signed Marians Pahars a year earlier – for £600,000.

[22] Moroccan centre-back Tahar El Khalej joined from Benfica the same month,[23] as did free midfielder Paul Hughes, who had played under Hoddle at Chelsea.

[27] This was followed by a second win from three when the Saints beat Newcastle United 4–2 at home, with second-half goals from Hassan Kachloul (two), Marians Pahars and Mark Hughes sending the South Coast side to 6th in the league table.

[27][28] Following the sale of Østenstad to Blackburn Rovers in exchange for the return of Kevin Davies, Southampton lost 1–4 at Everton but beat Sheffield Wednesday 2–0 at home to see out August.

[27][19] Two 3–3 draws followed, against defending league champions Manchester United at Old Trafford and at home to Derby County, the latter of which saw the Saints "carelessly surrender" the win by conceding twice late on.

[30] The winless run continued through October, as Southampton lost 1–2 at Leicester City, before sacrificing another four points from winning positions when they drew 1–1 with both Liverpool and Wimbledon.

[30] Against the third promoted side, Bradford City, Southampton won 1–0 at The Dell in their opening game of 2000, which helped them stay clear of the relegation zone at the Bantams' expense.

[32] After picking up their first win in two months over Bradford City, Southampton faced their joint-heaviest defeat of the season at Newcastle United, who were just one place above them in the table at the time.

Trailing 0–2 within three minutes, the Saints conceded two own goals courtesy of Richard Dryden and Garry Monk either side of half time to complete a 0–5 thrashing at St James' Park.

[34] In a statement about the change in manager, Southampton chairman Rupert Lowe assured fans that Jones had not been fired, but instead given a year away to "concentrate fully on his defence and the clearing of his name".

[24][39] They continued to pick up points against fellow strugglers, beating Bradford City 2–1 thanks to a goal from Pahars within 30 seconds of coming on as a substitute, and winning 2–0 against bottom-placed Watford.

[41] After the break, Southampton continued to enjoy the majority of chances, with Richards coming close to doubling their lead on 65 minutes when he headed in from a corner, but hit the crossbar.