| Club: | Middlesbrough |
| Season: | 1998–99 |
| Manager: | Bryan Robson |
| Chairman: | Steve Gibson |
| Stadium: | Riverside Stadium |
| League: | Premiership |
| League Result: | 9th |
| Cup1: | FA Cup |
| Cup1 Result: | Third round |
| Cup2: | Worthington Cup |
| Cup2 Result: | Third round |
| League Topscorer: | Ricard (15) |
| Season Topscorer: | Ricard (18) |
| Highest Attendance: | 34,687 (vs. Tottenham Hotspur, 20 February) |
| Lowest Attendance: | 11,531 (vs. Wycombe Wanderers, 16 September) |
| Average Attendance: | 34,386 |
| Prevseason: | 1997–98 |
| Nextseason: | 1999–2000 |
During the 1998–99 English football season, Middlesbrough competed in the FA Premier League (known as the FA Carling Premiership for sponsorship reasons).
Middlesbrough were the only newly promoted side to avoid relegation in 1998–99. They attained an impressive ninth-place finish in the final table - too high for relegation, but not quite high enough for a UEFA Cup place; they even rose as high as fourth by Christmas after a surprise 3–2 win at Old Trafford against champions Manchester United but they drew 15 games throughout the league season which ultimately prevented them from finishing any higher. Still, it was their highest finish for more than 20 years and a step in the right direction for manager Bryan Robson – who had come close to European qualification (via the cup competitions) in the previous two campaigns.
See main article: 1998–99 FA Premier League.
Middlesbrough's score comes first[1]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 15 August 1998 | Leeds United | H | 0–0 | 34,162 | ||
| 23 August 1998 | Aston Villa | A | 1–3 | 29,559 | Beck | |
| 29 August 1998 | Derby County | H | 1–1 | 34,121 | Ricard | |
| 9 September 1998 | Leicester City | A | 1–0 | 20,635 | Gascoigne | |
| 13 September 1998 | Tottenham Hotspur | A | 3–0 | 30,437 | Ricard (2), Kinder | |
| 19 September 1998 | Everton | H | 2–2 | 34,563 | Ricard (2) | |
| 26 September 1998 | Chelsea | A | 0–2 | 34,811 | ||
| 3 October 1998 | Sheffield Wednesday | H | 4–0 | 34,163 | Beck (2), Ricard, Gascoigne | |
| 17 October 1998 | Blackburn Rovers | H | 2–1 | 34,413 | Ricard (pen), Fleming | |
| 24 October 1998 | Wimbledon | A | 2–2 | 14,114 | Mustoe, Ricard | |
| 1 November 1998 | Nottingham Forest | H | 1–1 | 34,223 | Deane | |
| 7 November 1998 | Southampton | A | 3–3 | 15,202 | Gascoigne, Lundekvam (own goal), Festa | |
| 15 November 1998 | Charlton Athletic | A | 1–1 | 20,043 | Stamp | |
| 21 November 1998 | Coventry City | H | 2–0 | 34,293 | Gordon, Ricard | |
| 29 November 1998 | Arsenal | A | 1–1 | 38,075 | Deane | |
| 6 December 1998 | Newcastle United | H | 2–2 | 34,629 | Townsend, Cooper | |
| 12 December 1998 | West Ham United | H | 1–0 | 34,623 | Deane | |
| 19 December 1998 | Manchester United | A | 3–2 | 55,152 | Ricard, Gordon, Deane | |
| 26 December 1998 | Liverpool | H | 1–3 | 34,626 | Deane | |
| 28 December 1998 | Derby County | A | 1–2 | 32,726 | Beck | |
| 9 January 1999 | Aston Villa | H | 0–0 | 34,643 | ||
| 16 January 1999 | Leeds United | A | 0–2 | 37,473 | ||
| 30 January 1999 | Leicester City | H | 0–0 | 34,631 | ||
| 6 February 1999 | Liverpool | A | 1–3 | 44,384 | Stamp | |
| 17 February 1999 | Everton | A | 0–5 | 31,606 | ||
| 20 February 1999 | Tottenham Hotspur | H | 0–0 | 34,687 | ||
| 27 February 1999 | Sheffield Wednesday | A | 1–3 | 24,534 | Mustoe | |
| 14 March 1999 | Southampton | H | 3–0 | 33,387 | Beck, Ricard, Vickers | |
| 20 March 1999 | Nottingham Forest | A | 2–1 | 21,468 | Ricard, Deane | |
| 3 April 1999 | Blackburn Rovers | A | 0–0 | 27,482 | ||
| 5 April 1999 | Wimbledon | H | 3–1 | 33,999 | Ricard (2), Festa | |
| 10 April 1999 | Charlton Athletic | H | 2–0 | 34,529 | Ricard, Mustoe | |
| 14 April 1999 | Chelsea | H | 0–0 | 34,406 | ||
| 17 April 1999 | Coventry City | A | 2–1 | 19,231 | Kinder, Gordon | |
| 24 April 1999 | Arsenal | H | 1–6 | 34,630 | Armstrong | |
| 1 May 1999 | Newcastle United | A | 1–1 | 36,552 | Mustoe | |
| 9 May 1999 | Manchester United | H | 0–1 | 34,665 | ||
| 16 May 1999 | West Ham United | A | 0–4 | 25,902 |
See main article: 1998–99 FA Cup.
| R3 | 3 January 1999 | Manchester United | A | 1–3 | 52,232 | Townsend |
See main article: 1998–99 Football League Cup.
| R2 1st Leg | 16 September 1998 | Wycombe Wanderers | H | 2–0 | 11,531 | Ricard, Festa | |
| R2 2nd Leg | 22 September 1998 | Wycombe Wanderers | A | 1–1 (won 3–1 on agg) | 5,698 | Ricard | |
| R3 | 28 October 1998 | Everton | H | 2–3 | 20,748 | Summerbell, Ricard |
(Starting appearances + substitute appearances)
| No. | Pos. | Name | League | FA Cup | League Cup | Total | Discipline | ||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Apps | Goals | Apps | Goals | Apps | Goals | Apps | Goals | ||||||
| 1 | GK |  Mark Schwarzer | 34 | 0 | 1 | 0 | 0 | 0 | 35 | 0 | 1 | 0 | |
| 2 | DF |  Curtis Fleming | 12+2 | 1 | 1 | 0 | 1 | 0 | 14+2 | 1 | 2 | 0 | |
| 3 | DF | Dean Gordon | 38 | 3 | 1 | 0 | 2 | 0 | 41 | 3 | 3 | 0 | |
| 4 | DF | Steve Vickers | 30+1 | 1 | 0 | 0 | 3 | 0 | 33+1 | 1 | 5 | 0 | |
| 5 | DF |  Gianluca Festa | 25 | 2 | 0 | 0 | 2 | 1 | 27 | 3 | 9 | 0 | |
| 6 | DF | Gary Pallister | 26 | 0 | 1 | 0 | 0 | 0 | 27 | 0 | 5 | 0 | |
| 7 | MF | Robbie Mustoe | 32+1 | 4 | 1 | 0 | 1 | 0 | 34+1 | 4 | 8 | 1 | |
| 8 | MF | Paul Gascoigne | 25+1 | 3 | 1 | 0 | 2 | 0 | 28+1 | 3 | 13 | 0 | |
| 9 | FW | Marco Branca | 0+1 | 0 | 0 | 0 | 0 | 0 | 0+1 | 0 | 0 | 0 | |
| 10 | FW | Brian Deane | 24+2 | 6 | 1 | 0 | 0+1 | 0 | 25+3 | 6 | 3 | 0 | |
| 10 | MF | Paul Merson | 3 | 0 | 0 | 0 | 0 | 0 | 3 | 0 | 0 | 0 | |
| 11 | MF | Alan Moore | 3+1 | 0 | 0 | 0 | 1 | 0 | 4+1 | 0 | 0 | 0 | |
| 12 | FW | Mikkel Beck | 13+14 | 5 | 0+1 | 0 | 2 | 0 | 15+15 | 5 | 2 | 0 | |
| 13 | GK | Marlon Beresford | 4 | 0 | 0 | 0 | 3 | 0 | 7 | 0 | 0 | 0 | |
| 14 | MF | Phil Stamp | 5+11 | 2 | 0+1 | 0 | 3 | 0 | 8+12 | 2 | 1 | 1 | |
| 15 | MF | Neil Maddison | 10+10 | 0 | 1 | 0 | 1 | 0 | 12+10 | 0 | 1 | 0 | |
| 16 | MF | Andy Townsend | 35 | 1 | 1 | 1 | 1 | 0 | 37 | 2 | 10 | 0 | |
| 17 | DF |  Vladimír Kinder | 0+5 | 2 | 0 | 0 | 1 | 0 | 1+5 | 2 | 1 | 0 | |
| 18 | FW | Andy Campbell | 1+7 | 0 | 0 | 0 | 1+2 | 0 | 2+9 | 0 | 1 | 0 | |
| 19 | FW |  Hamilton Ricard | 32+4 | 15 | 1 | 0 | 3 | 3 | 36+4 | 18 | 6 | 0 | |
| 20 | FW | Alun Armstrong | 0+6 | 1 | 0 | 0 | 0 | 0 | 0+6 | 1 | 0 | 0 | |
| 21 | DF | Craig Harrison | 3+1 | 0 | 0 | 0 | 1+1 | 0 | 4+2 | 0 | 0 | 0 | |
| 22 | MF | Mark Summerbell | 7+4 | 0 | 0 | 0 | 0+2 | 1 | 7+6 | 1 | 4 | 0 | |
| 23 | DF | Clayton Blackmore | 0 | 0 | 0 | 0 | 1 | 0 | 1 | 0 | 0 | 0 | |
| 23 | MF | Keith O'Neill | 4+2 | 0 | 0 | 0 | 0 | 0 | 4+2 | 0 | 2 | 0 | |
| 24 | DF | Steve Baker | 1+1 | 0 | 0 | 0 | 0 | 0 | 1+1 | 0 | 0 | 0 | |
| 27 | MF | Anthony Ormerod | 0 | 0 | 0 | 0 | 0+1 | 0 | 0+1 | 0 | 0 | 0 | |
| 28 | DF | Robbie Stockdale | 17+2 | 0 | 0 | 0 | 3 | 0 | 20+2 | 0 | 4 | 0 | |
| 29 | DF | Colin Cooper | 32+1 | 1 | 1 | 0 | 1 | 0 | 34+1 | 1 | 5 | 0 | |
| 30 | MF | Micky Cummins | 1 | 0 | 0 | 0 | 0 | 0 | 1 | 0 | 0 | 0 | |
| 31 | DF | Jason Gavin | 2 | 0 | 0 | 0 | 0 | 0 | 2 | 0 | 0 | 0 | |
| Date | Pos. | Name | From | Fee | |
|---|---|---|---|---|---|
| 6 July 1998 | DF | Dean Gordon | Crystal Palace | £900,000 | |
| 6 July 1998 | DF | Gary Pallister | Manchester United | £2,500,000 | |
| 18 August 1998 | DF | Colin Cooper | Nottingham Forest | £2,500,000 | |
| 12 October 1998 | FW | Brian Deane | Benfica | £3,000,000 | |
| 18 March 1999 | MF | Keith O'Neill | Norwich City | £700,000 |
| Date | Pos. | Name | To | Fee | |
|---|---|---|---|---|---|
| 1 July 1998 | DF | Craig Liddle | Darlington | Free transfer | |
| 8 September 1998 | MF | Paul Merson | Aston Villa | £6,750,000 | |
| 25 February 1999 | DF | Clayton Blackmore | Barnsley | Free transfer | |
| 25 March 1999 | FW | Mikkel Beck | Derby County | £500,000 | |
| 25 March 1999 | FW | Kris Trevor | Gateshead | Free transfer | |
| 20 May 1999 | FW | Paul Connor | Stoke City | Free transfer |
Transfers in: £9,600,000
Transfers out: £7,250,000
Total spending: £2,350,000