Every competitive match Southampton played in 1998–99, in Premier League — 42 matches, 11 won, 10 drawn, 21 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 16 Aug 1998 | Premier League | H | Liverpool | Liverpool 1998–99 | 1–2 | Egil Østenstad 37 | 15,202 |
| 22 Aug 1998 | Premier League | A | Charlton Athletic | Charlton Athletic 1998–99 | 0–5 | 16,488 | |
| 29 Aug 1998 | Premier League | H | Nottingham Forest | Nottingham Forest 1998–99 | 1–2 | Matt Le Tissier 89 | 14,942 |
| 8 Sep 1998 | Premier League | A | Leeds United | Leeds United 1998–99 | 0–3 | 30,637 | |
| 12 Sep 1998 | Premier League | A | Newcastle United | Newcastle United 1998–99 | 0–4 | 36,454 | |
| 15 Sep 1998 | League Cup | A | Fulham | Fulham 1998–99 | 1–1 | James Beattie 62 | 10,222 |
| 19 Sep 1998 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 1–1 | Matt Le Tissier 64 | 15,204 |
| 23 Sep 1998 | League Cup | H | Fulham | Fulham 1998–99 | 0–1 | 11,645 | |
| 28 Sep 1998 | Premier League | A | West Ham United | West Ham United 1998–99 | 0–1 | 23,153 | |
| 3 Oct 1998 | Premier League | H | Manchester United | Manchester United 1998–99 | 0–3 | 15,251 | |
| 17 Oct 1998 | Premier League | A | Arsenal | Arsenal 1998–99 | 1–1 | David Howells 67 | 38,027 |
| 24 Oct 1998 | Premier League | H | Coventry City | Coventry City 1998–99 | 2–1 | Matt Le Tissier 23, Egil Østenstad 44 | 15,152 |
| 31 Oct 1998 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 0–0 | 30,078 | |
| 7 Nov 1998 | Premier League | H | Middlesbrough | Middlesbrough 1998–99 | 3–3 | Ken Monkou 61, James Beattie 82, Egil Østenstad 85 | 15,202 |
| 14 Nov 1998 | Premier League | H | Aston Villa | Aston Villa 1998–99 | 1–4 | Matt Le Tissier 53 | 15,242 |
| 21 Nov 1998 | Premier League | A | Blackburn Rovers | Blackburn Rovers 1998–99 | 2–0 | Matt Oakley 4, Steve Basham 89 | 22,812 |
| 28 Nov 1998 | Premier League | H | Derby County | Derby County 1998–99 | 0–1 | 14,762 | |
| 5 Dec 1998 | Premier League | A | Leicester City | Leicester City 1998–99 | 0–2 | 18,423 | |
| 12 Dec 1998 | Premier League | A | Everton | Everton 1998–99 | 0–1 | 32,073 | |
| 19 Dec 1998 | Premier League | H | Wimbledon | Wimbledon 1998–99 | 3–1 | Egil Østenstad 11, Hassan Kachloul 64, Egil Østenstad 68 | 14,354 |
| 26 Dec 1998 | Premier League | H | Chelsea | Chelsea 1998–99 | 0–2 | 15,253 | |
| 28 Dec 1998 | Premier League | A | Nottingham Forest | Nottingham Forest 1998–99 | 1–1 | Hassan Kachloul 48 | 23,456 |
| 2 Jan 1999 | FA Cup | H | Fulham | Fulham 1998–99 | 1–1 | Egil Østenstad 89 | 12,549 |
| 9 Jan 1999 | Premier League | H | Charlton Athletic | Charlton Athletic 1998–99 | 3–1 | Hassan Kachloul 8, Patrick Colleter 52, James Beattie 89 | 15,222 |
| 13 Jan 1999 | FA Cup | A | Fulham | Fulham 1998–99 | 0–1 | 17,448 | |
| 16 Jan 1999 | Premier League | A | Liverpool | Liverpool 1998–99 | 1–7 | Egil Østenstad 59 | 44,011 |
| 30 Jan 1999 | Premier League | H | Leeds United | Leeds United 1998–99 | 3–0 | Hassan Kachloul 31, Matt Oakley 62, Egil Østenstad 86 | 15,236 |
| 6 Feb 1999 | Premier League | A | Chelsea | Chelsea 1998–99 | 0–1 | 34,920 | |
| 20 Feb 1999 | Premier League | H | Newcastle United | Newcastle United 1998–99 | 2–1 | James Beattie 16, Jason Dodd 43 | 15,244 |
| 27 Feb 1999 | Premier League | A | Manchester United | Manchester United 1998–99 | 1–2 | Matt Le Tissier 90 | 55,316 |
| 2 Mar 1999 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 0–3 | 28,580 | |
| 6 Mar 1999 | Premier League | H | West Ham United | West Ham United 1998–99 | 1–0 | Hassan Kachloul 10 | 15,240 |
| 14 Mar 1999 | Premier League | A | Middlesbrough | Middlesbrough 1998–99 | 0–3 | 33,387 | |
| 20 Mar 1999 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 1–0 | Matt Le Tissier 41 | 15,201 |
| 3 Apr 1999 | Premier League | H | Arsenal | Arsenal 1998–99 | 0–0 | 15,255 | |
| 5 Apr 1999 | Premier League | A | Coventry City | Coventry City 1998–99 | 0–1 | 21,404 | |
| 10 Apr 1999 | Premier League | A | Aston Villa | Aston Villa 1998–99 | 0–3 | 32,203 | |
| 17 Apr 1999 | Premier League | H | Blackburn Rovers | Blackburn Rovers 1998–99 | 3–3 | Chris Marsden 22, Mark Hughes 61, Marians Pahars 85 | 15,209 |
| 24 Apr 1999 | Premier League | A | Derby County | Derby County 1998–99 | 0–0 | 26,557 | |
| 1 May 1999 | Premier League | H | Leicester City | Leicester City 1998–99 | 2–1 | Chris Marsden 36, James Beattie 74 | 15,228 |
| 8 May 1999 | Premier League | A | Wimbledon | Wimbledon 1998–99 | 2–0 | James Beattie 72, Robbie Earle 84 | 24,068 |
| 16 May 1999 | Premier League | H | Everton | Everton 1998–99 | 2–0 | Marians Pahars 24, Marians Pahars 68 | 15,254 |
39 of the goals in this season carry a named scorer.
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