The 1999–2000 Southampton F.C. season was the club's 99th season of competitive football, their 30th (and 22nd consecutive) in the top flight of English football, and their eighth in the FA Premier League. 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. Outside the league, they reached the fourth round of both the FA Cup and the League Cup. 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. Although the case against Jones was dismissed, Hoddle remained in charge after the season ended.

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. They also re-signed striker Kevin Davies, who returned from Blackburn Rovers in exchange for Egil Østenstad, the previous season's top scorer. Other new arrivals throughout the season included Portuguese winger Luís Boa Morte, Norwegian midfielder Jo Tessem, Latvian midfielder Imants Bleidelis, and Moroccan defender Tahar El Khalej. The club picked up regular victories throughout the campaign, remaining clear of the bottom three of the league table for the whole year. Their form was slightly better under Hoddle when he took over as manager, with their FA Premier League status for 2000–01 confirmed with five games left to play.

Outside the league, Southampton improved on their previous season's performances in both the FA Cup and the League Cup. In the former, the Saints made it past First Division promotion hopefuls Ipswich Town in the third round with a slender 1–0 victory. They were knocked out in the fourth round by the same scoreline at the hands of Aston Villa, who would end the season in the top six of the FA Premier League. In the League Cup, Southampton beat Manchester City in the second round, winning the second leg 4–3 after extra time following a goalless first leg. In the third round, they beat FA Premier League high-flyers Liverpool 2–1, thanks to a last-minute goal from Trond Egil Soltvedt. They were eliminated in the fourth round by Aston Villa, who beat the Saints 4–0 just over a month before also eliminating them from the FA Cup.

Southampton used 29 players during the 1999–2000 season and had 15 different goalscorers. Latvian striker Marians Pahars finished as the club's top goalscorer for the first time, scoring 13 goals in the FA Premier League – more than twice as many as the second-highest scorer, Kevin Davies, on six league goals. Dean Richards made the most appearances for the side during his first of two seasons at the club, playing in 40 of the team's 44 fixtures across all competitions, and was named Southampton F.C. Player of the Season at the end of the campaign. The average league attendance at The Dell during 1999–2000 was 15,132. 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.

Background and transfers

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. Danish goalkeeper Michael Stensgaard, who had joined from Copenhagen just seven months earlier, returned to his former club having failed to make an appearance for the Saints. The club's sole signings prior to the start of the league season were defenders Bruno Leal and Dean Richards, who arrived from Portuguese side Sporting and First Division side Wolverhampton Wanderers, respectively, on free transfers. The day after the second game in the league, Southampton signed Norwegian attacking midfielder Trond Egil Soltvedt from Coventry City for £300,000. He was followed just under a week later by striker Kevin Davies, who returned to the club having left for Blackburn Rovers the previous summer for a Saints record fee of £7.5 million; in exchange, Southampton's 1998–99 top scorer Egil Østenstad moved to the recently relegated Rovers. Ken Monkou left on the same day to join second-flight side Huddersfield Town on a free transfer, while Portuguese winger Luís Boa Morte arrived from Arsenal for a fee of £500,000 a week later.

Changes to the squad continued throughout much of the season. During September, the club sent Kevin Gibbens, Garry Monk, Andy Williams and Shayne Bradley all out on loans – all but Bradley to Stockport County, Bradley to Exeter City. Williams' loan was made permanent at the beginning of October. That same month, John Beresford was loaned out to Birmingham City, while Scott Marshall was loaned out – and eventually sold, for £250,000 – to Brentford. In November, Richard Dryden was sent out on loan to Stoke City, where he would spend much of the rest of the season over two separate spells. Also in November, the club made their sixth signing of the season when they brought in Norwegian midfielder Jo Tessem from Molde, against whom they'd played in pre-season, for £600,000. December saw the £50,000 sale of Scott Hiley to local rivals Portsmouth, 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.

In January, striker David Hirst was forced to retire from professional football due to a knee injury he had picked up during the 1998–99 pre-season period. He subsequently joined Sheffield-based non-league side Brunsmeer Athletic. 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. In March, striker Mark Hughes was offloaded to Everton on a free transfer after a disappointing 20-month stay at the club which delivered only two goals. Moroccan centre-back Tahar El Khalej joined from Benfica the same month, as did free midfielder Paul Hughes, who had played under Hoddle at Chelsea. Dryden started his second loan spell at Stoke City just before the transfer deadline, remaining until the end of the season.

Players transferred in NameNationalityClubDateFeeRef.Bruno Leal Sporting8 July 1999FreeDean Richards Wolverhampton Wanderers14 July 1999FreeTrond Egil Soltvedt Coventry City12 August 1999£300,000Kevin Davies Blackburn Rovers17 August 1999ExchangeLuís Boa Morte Arsenal25 August 1999£500,000Jo Tessem Molde20 November 1999£600,000Imants Bleidelis Skonto2 February 2000£600,000Tahar El Khalej Benfica10 March 2000£350,000Paul Hughes Chelsea23 March 2000Free

Players transferred out NameNationalityClubDateFeeRef.Stephen Jenkins Brentford10 June 1999FreeSteve Basham Preston North End15 June 1999£200,000Michael Stensgaard Copenhagen1 July 1999FreeKen Monkou Huddersfield Town17 August 1999FreeEgil Østenstad Blackburn Rovers17 August 1999ExchangeAndy Williams Swindon Town1 October 1999£65,000Scott Marshall Brentford29 October 1999£250,000Scott Hiley Portsmouth3 December 1999£50,000David Hirst Brunsmeer Athletic25 January 2000FreeMark Hughes Everton14 March 2000Free

Players loaned in NameNationalityClubDate fromDate toRef.Marco Almeida Sporting20 July 19999 December 1999

Players loaned out NameNationalityClubDate fromDate toRef.Kevin Gibbens Stockport County9 September 199930 September 1999Garry Monk Stockport County9 September 199930 September 1999Andy Williams Swindon Town9 September 199930 September 1999Shayne Bradley Exeter City17 September 19993 November 1999John Beresford Birmingham City6 October 199913 October 1999Scott Marshall Brentford15 October 199926 October 1999Richard Dryden Stoke City2 November 19997 December 199922 March 2000End of season

Pre-season friendlies Ahead of the 1999–2000 season, Southampton played seven pre-season friendlies. In the first two, the club faced Isthmian League side Aldershot Town and Conference side Kingstonian on the same day in July, winning 3–2 and 2–1, respectively. A few days later, they faced three local sides as part of a short Norwegian tour, winning 3–1 against Førde, drawing 1–1 with Molde, and losing 1–3 to Viking. Another defeat in Europe, 0–1 at Belgian side Lierse, was followed by a 3–0 win over Second Division side Reading, with Matt Le Tissier and Egil Østenstad (two) on the scoresheet for the visitors.

FA Premier League

For the first time since the 1988–89 season, Southampton won their opening league fixture at the start of the 1999–2000 campaign, beating Coventry City 1–0 at Highfield Road thanks to a late goal from the previous season's top scorer, Egil Østenstad. They lost their first home game 0–3 to Leeds United four days later, with Michael Bridges scoring a hat-trick. 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. 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. The side sat 9th in the table at the end of the month.

The club's form dipped dramatically starting in September, when they lost 2–3 at Middlesbrough and 0–1 at home to Arsenal. In the first game, new winger Luís Boa Morte was sent off in his debut for the club, after which the hosts overturned Southampton's 2–1 lead to make the most of the advantage; in the second, the tie was decided by Thierry Henry's first league goal for the Gunners, scored when he beat another debutant, loanee Marco Almeida, who was ultimately making his only appearance for the club. 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. 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. A first win in eight games, a late 1–0 victory over Aston Villa, ensured that the side held their position at 14th place in the table.

Southampton saw out 1999 with another poor run of form, failing to pick up a win in their last seven games of the calendar year. The only point they picked up during this period was in a goalless draw at home to Coventry City at the beginning of December. The first two games after the win over Aston Villa saw the Saints ending with ten men and conceding late goals – in a home tie against Tottenham Hotspur, they conceded in the 81st minute before Claus Lundekvam was sent off in the penultimate minute; and in an away trip to Leeds United, they saw Patrick Colleter dismissed in the 88th minute before conceding the only goal of the game in the 90th. Other defeats were faced at the hands of two sides recently promoted to the Premier League, as the Saints lost 0–2 at Sunderland and 2–3 at Watford. 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.