| 29 Dec 1999 |
Aston Villa
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 26 Dec 1999 |
Tottenham Hotspur
|
4–0
|
Watford
|
H
|
ENG · Premier League
|
| 22 Dec 1999 |
Newcastle United
|
6–1
|
Tottenham Hotspur
|
H
|
ENG · FA Cup
Round 3
|
| 18 Dec 1999 |
Middlesbrough
|
2–1
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 12 Dec 1999 |
Tottenham Hotspur
|
1–1
|
Newcastle United
|
D
|
ENG · FA Cup
Round 3
|
| 06 Dec 1999 |
Tottenham Hotspur
|
0–0
|
West Ham United
|
D
|
ENG · Premier League
|
| 01 Dec 1999 |
Fulham
|
3–1
|
Tottenham Hotspur
|
H
|
ENG · League Cup
Round 4
|
| 28 Nov 1999 |
Newcastle United
|
2–1
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 20 Nov 1999 |
Southampton
|
0–1
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 07 Nov 1999 |
Tottenham Hotspur
|
2–1
|
Arsenal
|
H
|
ENG · Premier League
|
| 31 Oct 1999 |
Sunderland
|
2–1
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 23 Oct 1999 |
Tottenham Hotspur
|
3–1
|
Manchester United
|
H
|
ENG · Premier League
|
| 16 Oct 1999 |
Derby County
|
0–1
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 13 Oct 1999 |
Tottenham Hotspur
|
3–1
|
Crewe Alexandra
|
H
|
ENG · League Cup
Round 3
|
| 03 Oct 1999 |
Tottenham Hotspur
|
2–3
|
Leicester City
|
A
|
ENG · Premier League
|
| 26 Sep 1999 |
Wimbledon
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 19 Sep 1999 |
Tottenham Hotspur
|
3–2
|
Coventry City
|
H
|
ENG · Premier League
|
| 12 Sep 1999 |
Bradford City
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 09 Sep 1999 |
1. FC Kaiserslautern
|
2–0
|
Tottenham Hotspur
|
H
|
ITL · UEFA Europa League
|
| 28 Aug 1999 |
Tottenham Hotspur
|
1–2
|
Leeds United
|
A
|
ENG · Premier League
|
| 25 Aug 1999 |
Tottenham Hotspur
|
1–0
|
1. FC Kaiserslautern
|
H
|
ITL · UEFA Europa League
|
| 21 Aug 1999 |
Sheffield Wednesday
|
1–2
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 19 Aug 1999 |
Zimbru Chișinău
|
0–0
|
Tottenham Hotspur
|
D
|
ITL · UEFA Europa League
|
| 14 Aug 1999 |
Tottenham Hotspur
|
3–2
|
Everton
|
H
|
ENG · Premier League
|
| 09 Aug 1999 |
Tottenham Hotspur
|
3–1
|
Newcastle United
|
H
|
ENG · Premier League
|
| 07 Aug 1999 |
West Ham United
|
1–0
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 05 Aug 1999 |
Tottenham Hotspur
|
3–0
|
Zimbru Chișinău
|
H
|
ITL · UEFA Europa League
|
| 16 May 1999 |
Manchester United
|
2–1
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 10 May 1999 |
Tottenham Hotspur
|
2–2
|
Chelsea
|
D
|
ENG · Premier League
|
| 05 May 1999 |
Tottenham Hotspur
|
1–3
|
Arsenal
|
A
|
ENG · Premier League
|
| 01 May 1999 |
Liverpool
|
3–2
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 24 Apr 1999 |
Tottenham Hotspur
|
1–2
|
West Ham United
|
A
|
ENG · Premier League
|
| 20 Apr 1999 |
Charlton Athletic
|
1–4
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 17 Apr 1999 |
Nottingham Forest
|
0–1
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 11 Apr 1999 |
Newcastle United
|
2–0
|
Tottenham Hotspur
|
H
|
ENG · FA Cup
Semi-final
|
| 05 Apr 1999 |
Newcastle United
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 03 Apr 1999 |
Tottenham Hotspur
|
0–2
|
Leicester City
|
A
|
ENG · Premier League
|
| 21 Mar 1999 |
Tottenham Hotspur
|
1–0
|
Leicester City
|
H
|
ENG · League Cup
Final
|
| 16 Mar 1999 |
Barnsley
|
0–1
|
Tottenham Hotspur
|
A
|
ENG · FA Cup
Round 6
|
| 13 Mar 1999 |
Tottenham Hotspur
|
1–0
|
Aston Villa
|
H
|
ENG · Premier League
|
| 10 Mar 1999 |
Leeds United
|
2–0
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 02 Mar 1999 |
Tottenham Hotspur
|
3–0
|
Southampton
|
H
|
ENG · Premier League
|
| 27 Feb 1999 |
Tottenham Hotspur
|
1–1
|
Derby County
|
D
|
ENG · Premier League
|
| 24 Feb 1999 |
Tottenham Hotspur
|
2–0
|
Leeds United
|
H
|
ENG · FA Cup
Round 5
|
| 20 Feb 1999 |
Middlesbrough
|
0–0
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 16 Feb 1999 |
Wimbledon
|
0–1
|
Tottenham Hotspur
|
A
|
ENG · League Cup
Semi-final · Leg 2
|
| 13 Feb 1999 |
Leeds United
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · FA Cup
Round 5
|
| 06 Feb 1999 |
Tottenham Hotspur
|
0–0
|
Coventry City
|
D
|
ENG · Premier League
|
| 02 Feb 1999 |
Tottenham Hotspur
|
3–0
|
Wimbledon
|
H
|
ENG · FA Cup
Round 4
|
| 30 Jan 1999 |
Blackburn Rovers
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 27 Jan 1999 |
Tottenham Hotspur
|
0–0
|
Wimbledon
|
D
|
ENG · League Cup
Semi-final · Leg 1
|
| 23 Jan 1999 |
Wimbledon
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · FA Cup
Round 4
|
| 16 Jan 1999 |
Tottenham Hotspur
|
0–0
|
Wimbledon
|
D
|
ENG · Premier League
|
| 09 Jan 1999 |
Sheffield Wednesday
|
0–0
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 02 Jan 1999 |
Tottenham Hotspur
|
5–2
|
Watford
|
H
|
ENG · FA Cup
Round 3
|
| 28 Dec 1998 |
Tottenham Hotspur
|
4–1
|
Everton
|
H
|
ENG · Premier League
|
| 26 Dec 1998 |
Coventry City
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 19 Dec 1998 |
Chelsea
|
2–0
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 12 Dec 1998 |
Tottenham Hotspur
|
2–2
|
Manchester United
|
D
|
ENG · Premier League
|
| 05 Dec 1998 |
Tottenham Hotspur
|
2–1
|
Liverpool
|
H
|
ENG · Premier League
|
| 02 Dec 1998 |
Tottenham Hotspur
|
3–1
|
Manchester United
|
H
|
ENG · League Cup
Round 5
|
| 28 Nov 1998 |
West Ham United
|
2–1
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 21 Nov 1998 |
Tottenham Hotspur
|
2–0
|
Nottingham Forest
|
H
|
ENG · Premier League
|
| 14 Nov 1998 |
Arsenal
|
0–0
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 10 Nov 1998 |
Liverpool
|
1–3
|
Tottenham Hotspur
|
A
|
ENG · League Cup
Round 4
|
| 07 Nov 1998 |
Aston Villa
|
3–2
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 02 Nov 1998 |
Tottenham Hotspur
|
2–2
|
Charlton Athletic
|
D
|
ENG · Premier League
|
| 27 Oct 1998 |
Northampton Town
|
1–3
|
Tottenham Hotspur
|
A
|
ENG · League Cup
Round 3
|
| 24 Oct 1998 |
Tottenham Hotspur
|
2–0
|
Newcastle United
|
H
|
ENG · Premier League
|
| 19 Oct 1998 |
Leicester City
|
2–1
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 03 Oct 1998 |
Derby County
|
0–1
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 26 Sep 1998 |
Tottenham Hotspur
|
3–3
|
Leeds United
|
D
|
ENG · Premier League
|
| 23 Sep 1998 |
Tottenham Hotspur
|
3–2
|
Brentford
|
H
|
ENG · League Cup
Round 2 · Leg 2
|
| 19 Sep 1998 |
Southampton
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 15 Sep 1998 |
Brentford
|
2–3
|
Tottenham Hotspur
|
A
|
ENG · League Cup
Round 2 · Leg 1
|
| 13 Sep 1998 |
Tottenham Hotspur
|
0–3
|
Middlesbrough
|
A
|
ENG · Premier League
|
| 09 Sep 1998 |
Tottenham Hotspur
|
2–1
|
Blackburn Rovers
|
H
|
ENG · Premier League
|
| 29 Aug 1998 |
Everton
|
0–1
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 22 Aug 1998 |
Tottenham Hotspur
|
0–3
|
Sheffield Wednesday
|
A
|
ENG · Premier League
|
| 15 Aug 1998 |
Wimbledon
|
3–1
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 10 May 1998 |
Tottenham Hotspur
|
1–1
|
Southampton
|
D
|
ENG · Premier League
|
| 02 May 1998 |
Wimbledon
|
2–6
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 25 Apr 1998 |
Tottenham Hotspur
|
2–0
|
Newcastle United
|
H
|
ENG · Premier League
|
| 18 Apr 1998 |
Barnsley
|
1–1
|
Tottenham Hotspur
|
D
|
ENG · Premier League
|
| 13 Apr 1998 |
Tottenham Hotspur
|
1–1
|
Coventry City
|
D
|
ENG · Premier League
|
| 11 Apr 1998 |
Chelsea
|
2–0
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 04 Apr 1998 |
Tottenham Hotspur
|
1–1
|
Everton
|
D
|
ENG · Premier League
|
| 28 Mar 1998 |
Crystal Palace
|
1–3
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 14 Mar 1998 |
Tottenham Hotspur
|
3–3
|
Liverpool
|
D
|
ENG · Premier League
|
| 04 Mar 1998 |
Leeds United
|
1–0
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 01 Mar 1998 |
Tottenham Hotspur
|
1–0
|
Bolton Wanderers
|
H
|
ENG · Premier League
|
| 21 Feb 1998 |
Sheffield Wednesday
|
1–0
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 14 Feb 1998 |
Tottenham Hotspur
|
1–1
|
Leicester City
|
D
|
ENG · Premier League
|
| 07 Feb 1998 |
Blackburn Rovers
|
0–3
|
Tottenham Hotspur
|
A
|
ENG · Premier League
|
| 04 Feb 1998 |
Barnsley
|
3–1
|
Tottenham Hotspur
|
H
|
ENG · FA Cup
Round 4
|
| 31 Jan 1998 |
Derby County
|
2–1
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 24 Jan 1998 |
Tottenham Hotspur
|
1–1
|
Barnsley
|
D
|
ENG · FA Cup
Round 4
|
| 17 Jan 1998 |
Tottenham Hotspur
|
1–0
|
West Ham United
|
H
|
ENG · Premier League
|
| 10 Jan 1998 |
Manchester United
|
2–0
|
Tottenham Hotspur
|
H
|
ENG · Premier League
|
| 05 Jan 1998 |
Tottenham Hotspur
|
3–1
|
Fulham
|
H
|
ENG · FA Cup
Round 3
|
