| Club: | Barnsley |
| Season: | 1999–2000 |
| Manager: | Dave Bassett |
| Chairman: | John Dennis |
| Stadium: | Oakwell |
| League: | First Division |
| League Result: | 4th (qualified for play-offs) |
| Cup1: | Play-offs |
| Cup1 Result: | Runners-up |
| Cup2: | FA Cup |
| Cup2 Result: | Third round |
| Cup3: | League Cup |
| Cup3 Result: | Fourth round |
| League Topscorer: | Craig Hignett (19) |
| Average Attendance: | 15,412 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
During the 1999–2000 English football season, Barnsley F.C. competed in the Football League First Division.
Barnsley qualified for the play-offs and, after thrashing Birmingham City 5–2 on aggregate (with a 2–1 defeat at Oakwell insufficient for Birmingham to best Barnsley over two legs after the Tykes' 4–0 win at St Andrew's), reached the final at Wembley to face Ipswich Town. Barnsley took the lead through an own goal by Ipswich goalkeeper Richard Wright, but goals from Tony Mowbray, Richard Naylor and Marcus Stewart put Ipswich 3–1 up. A Craig Hignett penalty with twelve minutes left gave Barnsley hope, until Martijn Reuser's goal on the stroke of injury time. The 4–2 defeat condemned Barnsley to a second consecutive season in the First Division.
Barnsley, who were the Football League's top scorers with 88 goals, could have achieved automatic promotion, but for their poor defence that conceded 67 goals – the worst of any in the top twelve of the First Division, and joint fourth-worst in the division.
See main article: 1999–2000 Football League.
Barnsley's score comes first[1]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 7 August 1999 | Charlton Athletic | A | 1–3 | 19,268 | Barnard | |
| 14 August 1999 | Crystal Palace | H | 2–3 | 14,461 | Barnard (pen), Sheron | |
| 21 August 1999 | Blackburn Rovers | A | 2–1 | 19,537 | Hristov, Shipperley | |
| 28 August 1999 | Portsmouth | H | 6–0 | 13,792 | Van Der Lann (2), Barnard, Appleby (2), Hignett | |
| 30 August 1999 | Ipswich Town | A | 1–6 | 18,037 | McClare | |
| 3 September 1999 | Tranmere Rovers | H | 3–0 | 12,865 | Sheron, Dyer, McClare | |
| 10 September 1999 | Stockport County | H | 2–1 | 13,173 | Sheron (2) | |
| 18 September 1999 | Bolton Wanderers | A | 2–2 | 14,621 | Hignett, Barnard | |
| 25 September 1999 | Huddersfield Town | H | 4–2 | 17,765 | Barnard (2 pens), Sheron, Hignett | |
| 1 October 1999 | Nottingham Forest | A | 0–3 | 15,255 | ||
| 16 October 1999 | Wolverhampton Wanderers | H | 1–2 | 14,923 | Hignett | |
| 19 October 1999 | Swindon Town | H | 1–0 | 12,026 | Thomas | |
| 23 October 1999 | Crewe Alexandra | A | 1–0 | 5,421 | Hignett | |
| 26 October 1999 | Huddersfield Town | A | 1–2 | 15,764 | Sheron | |
| 30 October 1999 | Nottingham Forest | H | 1–0 | 14,727 | Hignett (pen) | |
| 6 November 1999 | Sheffield United | H | 2–0 | 16,301 | Shipperley (2) | |
| 13 November 1999 | Fulham | A | 3–1 | 10,634 | Symons (own goal), Dyer, Van Der Lann | |
| 20 November 1999 | Birmingham City | H | 2–1 | 14,520 | Tinkler, Hignett (pen) | |
| 24 November 1999 | Manchester City | A | 1–3 | 32,692 | Thomas | |
| 27 November 1999 | Queens Park Rangers | A | 2–2 | 11,054 | Thomas, Eaden | |
| 4 December 1999 | Charlton Athletic | H | 1–1 | 14,553 | Chettle | |
| 18 December 1999 | Walsall | H | 3–2 | 13,300 | Hignett (3) | |
| 26 December 1999 | Grimsby Town | A | 3–0 | 8,742 | Hignett (2), Appleby | |
| 28 December 1999 | Port Vale | H | 3–1 | 16,855 | Tinkler, Barnard, Shipperley | |
| 3 January 2000 | West Bromwich Albion | A | 2–0 | 13,411 | Barnard (2) | |
| 8 January 2000 | Norwich City | A | 2–2 | 14,039 | Dyer, Hignett | |
| 15 January 2000 | Crystal Palace | A | 2–0 | 14,225 | Dyer, Barnard (pen) | |
| 22 January 2000 | Blackburn Rovers | H | 5–1 | 18,088 | Dyer (2), Hignett, Shipperley, Barnard | |
| 29 January 2000 | Portsmouth | A | 0–3 | 12,201 | ||
| 5 February 2000 | Ipswich Town | H | 0–2 | 17,601 | ||
| 11 February 2000 | Tranmere Rovers | H | 2–2 | 7,127 | Shipperley, Thomas | |
| 19 February 2000 | Queens Park Rangers | H | 1–1 | 14,212 | Hignett (pen) | |
| 26 February 2000 | Bolton Wanderers | H | 1–1 | 14,604 | Tinkler | |
| 3 March 2000 | Stockport County | A | 3–1 | 6,386 | Hristov (2), Shipperley | |
| 7 March 2000 | Sheffield United | A | 3–3 | 22,376 | Hristov, Barnard (pen), Shipperley | |
| 11 March 2000 | Manchester City | H | 2–1 | 22,650 | Curtis, Hignett | |
| 18 March 2000 | Birmingham City | A | 1–3 | 25,108 | Hignett | |
| 21 March 2000 | Fulham | H | 1–0 | 14,262 | Shipperley | |
| 27 March 2000 | Grimsby Town | H | 3–0 | 14,613 | Tinkler, Shipperley, Hignett | |
| 1 April 2000 | Walsall | A | 4–1 | 7,218 | Sheron (2), Shipperley, Appleby | |
| 8 April 2000 | West Bromwich Albion | H | 2–2 | 16,329 | Barnard, Shipperley | |
| 15 April 2000 | Port Vale | A | 2–2 | 5,918 | Hignett, Curtis | |
| 22 April 2000 | Wolverhampton Wanderers | A | 0–2 | 21,251 | ||
| 24 April 2000 | Norwich City | H | 2–1 | 15,253 | Chettle, Shipperley | |
| 29 April 2000 | Swindon Town | A | 2–1 | 6,151 | Appleby, Sheron | |
| 7 May 2000 | Crewe Alexandra | H | 0–2 | 17,611 |
| SF 1st Leg | 13 May 2000 | Birmingham City | A | 4–0 | 26,492 | Shipperley, Dyer (2), Hignett | |
| SF 2nd Leg | 18 May 2000 | Birmingham City | H | 1–2 (won 5–2 on agg) | 19,050 | Dyer | |
| F | 29 May 2000 | Ipswich Town | N | 2–4 | 73,427 | Wright (own goal), Hignett |
See main article: 1999–2000 FA Cup.
| R3 | 11 December 1999 | Wimbledon | A | 0–1 | 4,505 |
See main article: 1999–2000 Football League Cup.
| R1 1st Leg | 10 August 1999 | Lincoln City | A | 4–2 | 3,426 | Shipperley, Van Der Lann, Eaden | |
| R1 2nd Leg | 24 August 1999 | Lincoln City | H | 2–2 (won 6–4 on agg) | 7,047 | Sheron, Eaden | |
| R2 1st Leg | 14 September 1999 | Stockport County | H | 1–1 | 6,966 | Barnard | |
| R2 2nd Leg | 21 September 1999 | Stockport County | A | 3–3 (won on away goals) | 3,332 | Hristov (2), Jones | |
| R3 | 12 October 1999 | Bradford City | A | 3–2 | 8,583 | Sheron, Morgan, Barnard (pen) | |
| R4 | 30 November 1999 | Tranmere Rovers | A | 0–4 | 7,039 |