Every competitive match Southampton played in 1898–99, in Southern League — 27 matches, 17 won, 5 drawn, 5 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 3 Sep 1898 | Other | H | Brighton United | 4–1 | Watty Keay, Abe Hartley, Jim McKenzie, Tom Smith | ||
| 17 Sep 1898 | Other | H | New Brompton | 0–2 | |||
| 24 Sep 1898 | Other | A | Gravesend United | 2–1 | Abe Hartley, Bob Petrie | ||
| 1 Oct 1898 | Other | H | Millwall | 2–0 | Harry Wood, Harry Wood | ||
| 8 Oct 1898 | Other | H | Royal Artillery Portsmouth | 4–1 | Abe Hartley, Jim McKenzie, Samuel Meston, Harry Wood | ||
| 15 Oct 1898 | Other | H | Reading | 0–0 | |||
| 22 Oct 1898 | Other | A | Swindon Town | 1–1 | Abe Hartley | ||
| 5 Nov 1898 | Other | H | Gravesend United | 4–1 | Abe Hartley, Watty Keay, Jim McKenzie, Harry Wood | ||
| 12 Nov 1898 | Other | H | Sheppey United | 6–0 | Harry Wood, Harry Wood, Harry Wood, Abe Hartley, Abe Hartley, Watty Keay | ||
| 26 Nov 1898 | Other | A | Millwall | 4–1 | Abe Hartley, Abe Hartley, Arthur Chadwick, Watty Keay | ||
| 17 Dec 1898 | Other | A | Royal Artillery Portsmouth | 1–1 | Watty Keay | ||
| 24 Dec 1898 | Other | H | Swindon Town | 4–1 | Harry Wood, Harry Wood, Abe Hartley, Watty Keay | ||
| 26 Dec 1898 | Other | H | Tottenham Hotspur | Tottenham Hotspur 1898–99 | 1–1 | Harry Wood | |
| 31 Dec 1898 | Other | H | Bedminster | 1–0 | Harry Wood | ||
| 7 Jan 1899 | Other | A | Sheppey United | 1–2 | George Seeley | ||
| 28 Jan 1899 | FA Cup | A | New Brompton | 1–0 | Abe Hartley | 5,000 | |
| 11 Feb 1899 | FA Cup | A | Notts County | Notts County 1898–99 | 1–0 | Abe Hartley | 18,000 |
| 18 Feb 1899 | Other | A | Reading | 0–2 | |||
| 25 Feb 1899 | FA Cup | H | Derby County | Derby County 1898–99 | 1–2 | Tom Nicol | 14,000 |
| 11 Mar 1899 | Other | H | Bristol City | Bristol City 1898–99 | 4–1 | Abe Hartley, Abe Hartley, Abe Hartley, Tom Nicol | |
| 18 Mar 1899 | Other | H | Chatham Town | 4–1 | Abe Hartley, Duncan McLean, Harry Wood | ||
| 27 Mar 1899 | Other | A | Brighton United | 2–0 | David Steven, David Steven | ||
| 31 Mar 1899 | Other | A | Tottenham Hotspur | Tottenham Hotspur 1898–99 | 1–0 | Harry Wood | |
| 4 Apr 1899 | Other | A | Bedminster | 1–2 | Harry Haynes | ||
| 22 Apr 1899 | Other | A | Chatham Town | 2–1 | Duncan McLean, Harry Wood | ||
| 24 Apr 1899 | Other | A | New Brompton | 1–1 | Harry Haynes | ||
| 29 Apr 1899 | Other | A | Bristol City | Bristol City 1898–99 | 4–3 | Harry Wood, Harry Wood, Arthur Chadwick, Duncan McLean |
56 of the goals in this season carry a named scorer.
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