| Club: | Southend United |
| Season: | 1991–92 |
| Manager: | David Webb |
| Chairman: | Vic Jobson |
| Stadium: | Roots Hall |
| League: | Second Division |
| League Result: | 12th |
| Cup1: | FA Cup |
| Cup1 Result: | Third round |
| Cup2: | League Cup |
| Cup2 Result: | First round |
| Cup3: | Full Members Cup |
| Cup3 Result: | Second round |
| League Topscorer: | Angell (21) |
| Season Topscorer: | Angell (23) |
| Average Attendance: | 6,733 |
| Prevseason: | 1990–91 |
| Nextseason: | 1992–93 |
During the 1991–92 English football season, Southend United F.C. competed in the Football League Second Division.
In the 1991–92 season, Southend finished 12th in the old Second Division, their highest ever position in the Football League to date. On New Year's Day 1992, Southend briefly topped the Second Division but their dreary late season form stopped any hopes of a unique third successive promotion that would have given them a place as a Premier League founder member. Manager David Webb then stepped down.
See main article: 1991–92 Football League.
Southend United's score comes first[1]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 17 August 1991 | Bristol City | H | 1–1 | 6,720 | Benjamin | |
| 24 August 1991 | Derby County | A | 2–1 | 12,284 | Sussex, Angell | |
| 31 August 1991 | Leicester City | H | 1–2 | 6,944 | Martin | |
| 3 September 1991 | Cambridge United | A | 1–0 | 6,413 | Benjamin | |
| 7 September 1991 | Ipswich Town | A | 0–1 | 12,732 | ||
| 14 September 1991 | Bristol Rovers | H | 2–0 | 4,670 | Ansah, Angell | |
| 17 September 1991 | Plymouth Argyle | H | 2–1 | 4,585 | Angell, Benjamin | |
| 21 September 1991 | Port Vale | A | 0–0 | 5,988 | ||
| 28 September 1991 | Wolverhampton Wanderers | H | 0–2 | 8,368 | ||
| 4 October 1991 | Tranmere Rovers | A | 1–1 | 7,358 | Angell | |
| 12 October 1991 | Millwall | H | 2–3 | 7,266 | Sussex, Tilson | |
| 19 October 1991 | Watford | A | 2–1 | 6,862 | Sussex, Dublin (own goal) | |
| 26 October 1991 | Charlton Athletic | H | 1–1 | 7,320 | Austin (pen) | |
| 30 October 1991 | Oxford United | H | 2–3 | 4,873 | Angell, Tilson | |
| 2 November 1991 | Middlesbrough | A | 1–1 | 9,664 | Angell | |
| 5 November 1991 | Blackburn Rovers | H | 3–0 | 4,860 | Angell (2), Benjamin | |
| 9 November 1991 | Swindon Town | H | 3–2 | 7,709 | Angell (2), Tilson | |
| 20 November 1991 | Newcastle United | A | 2–3 | 14,740 | Angell, Tilson | |
| 23 November 1991 | Barnsley | H | 2–1 | 5,060 | Angell, Tilson | |
| 30 November 1991 | Sunderland | A | 2–1 | 13,575 | Angell, Scully | |
| 7 December 1991 | Brighton & Hove Albion | H | 2–1 | 6,303 | Ansah, Tilson | |
| 14 December 1991 | Portsmouth | A | 1–1 | 9,006 | Scully | |
| 22 December 1991 | Cambridge United | H | 1–1 | 9,353 | Benjamin | |
| 26 December 1991 | Oxford United | A | 1–0 | 5,601 | Angell | |
| 28 December 1991 | Leicester City | A | 0–2 | 15,635 | ||
| 1 January 1992 | Newcastle United | H | 4–0 | 9,458 | Angell (2), Jones, Ansah | |
| 11 January 1992 | Derby County | H | 1–0 | 8,295 | Ansah | |
| 18 January 1992 | Bristol City | A | 2–2 | 9,883 | Angell, Ansah | |
| 1 February 1992 | Watford | H | 1–0 | 7,581 | Benjamin | |
| 8 February 1992 | Charlton Athletic | A | 0–2 | 9,724 | ||
| 15 February 1992 | Barnsley | A | 0–1 | 5,328 | ||
| 18 February 1992 | Grimsby Town | A | 2–3 | 5,337 | Austin, Ansah | |
| 22 February 1992 | Sunderland | H | 2–0 | 7,473 | Angell, Jones | |
| 29 February 1992 | Brighton & Hove Albion | A | 2–3 | 8,271 | Benjamin, Angell | |
| 10 March 1992 | Blackburn Rovers | A | 2–2 | 14,404 | Ansah, Angell | |
| 14 March 1992 | Middlesbrough | H | 0–1 | 7,272 | ||
| 17 March 1992 | Portsmouth | H | 2–3 | 6,832 | Tilson, Jones | |
| 21 March 1992 | Swindon Town | A | 1–3 | 8,628 | Ansah | |
| 28 March 1992 | Grimsby Town | H | 3–1 | 4,591 | Angell, Scully, Ansah | |
| 1 April 1992 | Bristol Rovers | A | 1–0 | 5,375 | Jones | |
| 4 April 1992 | Ipswich Town | H | 1–2 | 10,003 | Prior | |
| 11 April 1992 | Plymouth Argyle | A | 2–0 | 7,060 | Marker (own goal), Benjamin | |
| 15 April 1992 | Port Vale | H | 0–0 | 4,462 | ||
| 20 April 1992 | Wolverhampton Wanderers | A | 1–3 | 10,953 | Benjamin | |
| 25 April 1992 | Tranmere Rovers | H | 1–1 | 4,761 | Jones | |
| 2 May 1992 | Millwall | A | 0–2 | 7,574 |
See main article: 1991-92 FA Cup.
| R3 | 4 January 1992 | Everton | A | 0–1 | 22,605 |
See main article: 1991–92 Football League Cup.
| R1 1st Leg | 20 August 1991 | Watford | A | 0–2 | 6,231 | ||
| R1 2nd Leg | 28 August 1991 | Watford | H | 1–1 (lost 1–3 on agg) | 3,802 | Angell |
See main article: 1991-92 Full Members Cup.
| SR1 | 2 October 1991 | Watford | A | 1–0 | 1,700 | Sussex | |
| SR2 | 22 October 1991 | Crystal Palace | A | 2–4 | 7,185 | Jones, Angell |