| Club: | Middlesbrough |
| Season: | 1999–2000 |
| Chairman: | Steve Gibson |
| Manager: | Bryan Robson |
| Stadium: | Riverside Stadium |
| League: | Premier League |
| League Result: | 12th |
| Cup1: | FA Cup |
| Cup1 Result: | Third round |
| Cup2: | League Cup |
| Cup2 Result: | Quarter-finals |
| League Topscorer: | Ricard (12) |
| Season Topscorer: | Ricard (14) |
| Highest Attendance: | 34,800 vs Leeds United (26 February, Premier League) |
| Lowest Attendance: | 8,843 vs Watford (13 October, League Cup) |
| Average Attendance: | 33,263 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
During the 1999–2000 season, Middlesbrough participated in the FA Premier League.
Middlesbrough experienced another satisfactory season, finishing 12th in the Premiership. They never looked like qualifying for Europe, but were never in any danger of relegation. Nor did they make much of an impact in the cup competitions.
Middlesbrough's kit was produced by Errea. The home shirt consisted of a red shirt with vertical navy and white stripes (repeated diagonally on the arms), white shorts with red stripes and red socks with navy and white trim. The away strip consisted of a white shirt with purple hoop framed with a black line, purple collar and shoulder bars, again with black trim, white shorts trimmed with purple and black and white purple topped socks.[1]
Middlesbrough were again sponsored by BT Cellnet.
See main article: 1999–2000 FA Premier League.
Middlesbrough's score comes firstc
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 7 August 1999 | Bradford City | H | 0–1 | 33,762 | ||
| 10 August 1999 | Wimbledon | A | 3–2 | 11,036 | Ziege, Ricard (2, 1 pen) | |
| 14 August 1999 | Derby County | A | 3–1 | 24,045 | Deane, Ziege, Ricard (pen) | |
| 21 August 1999 | Liverpool | H | 1–0 | 34,783 | Deane | |
| 24 August 1999 | Leicester City | H | 0–3 | 33,126 | ||
| 28 August 1999 | Aston Villa | A | 0–1 | 28,728 | ||
| 11 September 1999 | Southampton | H | 3–2 | 32,165 | Pallister, Gascoigne (pen), Deane | |
| 19 September 1999 | Leeds United | A | 0–2 | 34,122 | ||
| 25 September 1999 | Chelsea | H | 0–1 | 34,183 | ||
| 3 October 1999 | Newcastle United | A | 1–2 | 36,421 | Deane | |
| 17 October 1999 | West Ham United | H | 2–0 | 31,862 | Deane, Armstrong | |
| 24 October 1999 | Watford | A | 3–1 | 16,081 | Williams (own goal), Juninho, Ince | |
| 30 October 1999 | Everton | H | 2–1 | 33,916 | Ziege, Deane | |
| 6 November 1999 | Sunderland | H | 1–1 | 34,793 | Ricard | |
| 20 November 1999 | Arsenal | A | 1–5 | 38,082 | Ricard | |
| 27 November 1999 | Wimbledon | H | 0–0 | 31,400 | ||
| 4 December 1999 | Bradford City | A | 1–1 | 17,708 | Ricard | |
| 18 December 1999 | Tottenham Hotspur | H | 2–1 | 33,129 | Ziege, Deane | |
| 26 December 1999 | Sheffield Wednesday | A | 0–1 | 28,531 | ||
| 15 January 2000 | Derby County | H | 1–4 | 32,745 | Campbell | |
| 22 January 2000 | Liverpool | A | 0–0 | 44,324 | ||
| 29 January 2000 | Manchester United | A | 0–1 | 61,267 | ||
| 5 February 2000 | Leicester City | A | 1–2 | 17,550 | Campbell | |
| 14 February 2000 | Aston Villa | H | 0–4 | 31,571 | ||
| 19 February 2000 | Coventry City | H | 2–0 | 32,798 | Festa, Ricard | |
| 26 February 2000 | Leeds United | H | 0–0 | 34,800 | ||
| 4 March 2000 | Southampton | A | 1–1 | 15,223 | Ricard (pen) | |
| 12 March 2000 | Arsenal | H | 2–1 | 34,244 | Ince, Ricard | |
| 18 March 2000 | Sunderland | A | 1–1 | 42,013 | Ziege | |
| 25 March 2000 | Sheffield Wednesday | H | 1–0 | 32,748 | Campbell | |
| 3 April 2000 | Tottenham Hotspur | A | 3–2 | 31,796 | Carr (own goal), Ricard (2) | |
| 10 April 2000 | Manchester United | H | 3–4 | 34,775 | Campbell, Ince, Juninho | |
| 15 April 2000 | Coventry City | A | 1–2 | 19,435 | Ziege (pen) | |
| 22 April 2000 | Chelsea | A | 1–1 | 34,467 | Ricard | |
| 29 April 2000 | West Ham United | A | 1–0 | 25,472 | Deane (pen) | |
| 2 May 2000 | Newcastle United | H | 2–2 | 34,744 | Juninho, Festa | |
| 6 May 2000 | Watford | H | 1–1 | 32,930 | Stockdale | |
| 14 May 2000 | Everton | A | 2–0 | 34,663 | Deane, Juninho |
See main article: 1999–2000 FA Cup.
| R3 | 11 December 1999 | Wrexham | A | 1–2 | 11,755 | Deane |
See main article: 1999–2000 Football League Cup.
| R2 1st Leg | 14 September 1999 | Chesterfield | A | 0–0 | 4,941 | ||
| R2 2nd Leg | 21 September 1999 | Chesterfield | H | 2–1 (won 2-1 on agg) | 25,602 | Ince, Vickers | |
| R3 | 13 October 1999 | Watford | H | 1–0 | 8,843 | Juninho | |
| R4 | 30 November 1999 | Arsenal | H | 2–2 (won 3-1 on pens) | 23,157 | Ricard (2, 1 pen) | |
| R5 | 14 December 1999 | Tranmere Rovers | A | 1–2 | 10,581 | Ziege |
| Date | Pos. | Name | From | Fee | |
|---|---|---|---|---|---|
| 30 July 1999 | MF | Paul Ince | Liverpool | £1,000,000 | |
| 31 July 1999 | DF | Christian Ziege | A.C. Milan | £4,000,000 | |
| 27 October 1999 | MF | Carlos Marinelli | Boca Juniors | £1,500,000 | |
| 23 March 2000 | FW | Arthuro | Criciúma | Free transfer |
| Date | Pos. | Name | To | Fee | |
|---|---|---|---|---|---|
| 17 September 1999 | MF | Andy Townsend | West Bromwich Albion | £50,000 | |
| 17 March 2000 | MF | Micky Cummins | Port Vale | Free |
Transfers in: £6,500,000
Transfers out: £50,000
Total spending: £6,450,000
Goalscoring statistics for 1999–2000.[3]
 Hamilton Ricard | 12 | 0 | 2 | 14 | |
| Brian Deane | 9 | 1 | 0 | 10 | |
 Christian Ziege | 6 | 0 | 1 | 7 | |
 Juninho | 4 | 0 | 1 | 5 | |
| Andy Campbell | 4 | 0 | 0 | 4 | |
| Paul Ince | 3 | 0 | 1 | 4 | |
 Gianluca Festa | 2 | 0 | 0 | 2 | |
| Gary Pallister | 1 | 0 | 0 | 1 | |
| Paul Gascoigne | 1 | 0 | 0 | 1 | |
| Alun Armstrong | 1 | 0 | 0 | 1 | |
| Robbie Stockdale | 1 | 0 | 0 | 1 | |
| Steve Vickers | 0 | 0 | 1 | 1 | |
| Own goals | 2 | 0 | 0 | 2 |
