| 30 Oct 1999 |
Derby County
|
3–1
|
Chelsea
|
H
|
ENG · Premier League
|
| 26 Oct 1999 |
AC Milan
|
1–1
|
Chelsea
|
D
|
ITL · UEFA Champions League
Group stage
|
| 23 Oct 1999 |
Chelsea
|
2–3
|
Arsenal
|
A
|
ENG · Premier League
|
| 20 Oct 1999 |
Galatasaray SK
|
0–5
|
Chelsea
|
A
|
ITL · UEFA Champions League
Group stage
|
| 16 Oct 1999 |
Liverpool
|
1–0
|
Chelsea
|
H
|
ENG · Premier League
|
| 13 Oct 1999 |
Chelsea
|
0–1
|
Huddersfield Town
|
A
|
ENG · League Cup
Round 3
|
| 03 Oct 1999 |
Chelsea
|
5–0
|
Manchester United
|
H
|
ENG · Premier League
|
| 28 Sep 1999 |
Chelsea
|
1–0
|
Galatasaray SK
|
H
|
ITL · UEFA Champions League
Group stage
|
| 25 Sep 1999 |
Middlesbrough
|
0–1
|
Chelsea
|
A
|
ENG · Premier League
|
| 21 Sep 1999 |
Hertha BSC
|
2–1
|
Chelsea
|
H
|
ITL · UEFA Champions League
Group stage
|
| 18 Sep 1999 |
Watford
|
1–0
|
Chelsea
|
H
|
ENG · Premier League
|
| 15 Sep 1999 |
Chelsea
|
0–0
|
AC Milan
|
D
|
ITL · UEFA Champions League
Group stage
|
| 11 Sep 1999 |
Chelsea
|
1–0
|
Newcastle United
|
H
|
ENG · Premier League
|
| 28 Aug 1999 |
Wimbledon
|
0–1
|
Chelsea
|
A
|
ENG · Premier League
|
| 25 Aug 1999 |
Skonto Riga
|
0–0
|
Chelsea
|
D
|
ITL · UEFA Champions League
Qualifying · Leg 2
|
| 21 Aug 1999 |
Chelsea
|
1–0
|
Aston Villa
|
H
|
ENG · Premier League
|
| 14 Aug 1999 |
Leicester City
|
2–2
|
Chelsea
|
D
|
ENG · Premier League
|
| 11 Aug 1999 |
Chelsea
|
3–0
|
Skonto Riga
|
H
|
ITL · UEFA Champions League
Qualifying · Leg 1
|
| 07 Aug 1999 |
Chelsea
|
4–0
|
Sunderland
|
H
|
ENG · Premier League
|
| 16 May 1999 |
Chelsea
|
2–1
|
Derby County
|
H
|
ENG · Premier League
|
| 10 May 1999 |
Tottenham Hotspur
|
2–2
|
Chelsea
|
D
|
ENG · Premier League
|
| 05 May 1999 |
Chelsea
|
1–0
|
Leeds United
|
H
|
ENG · Premier League
|
| 01 May 1999 |
Chelsea
|
3–1
|
Everton
|
H
|
ENG · Premier League
|
| 25 Apr 1999 |
Sheffield Wednesday
|
0–0
|
Chelsea
|
D
|
ENG · Premier League
|
| 22 Apr 1999 |
RCD Mallorca
|
1–0
|
Chelsea
|
H
|
ITL · UEFA Cup Winners' Cup
Semi-final · Leg 2
|
| 18 Apr 1999 |
Chelsea
|
2–2
|
Leicester City
|
D
|
ENG · Premier League
|
| 14 Apr 1999 |
Middlesbrough
|
0–0
|
Chelsea
|
D
|
ENG · Premier League
|
| 11 Apr 1999 |
Wimbledon
|
1–2
|
Chelsea
|
A
|
ENG · Premier League
|
| 08 Apr 1999 |
Chelsea
|
1–1
|
RCD Mallorca
|
D
|
ITL · UEFA Cup Winners' Cup
Semi-final · Leg 1
|
| 03 Apr 1999 |
Charlton Athletic
|
0–1
|
Chelsea
|
A
|
ENG · Premier League
|
| 21 Mar 1999 |
Aston Villa
|
0–3
|
Chelsea
|
A
|
ENG · Premier League
|
| 18 Mar 1999 |
Vålerenga Fotball
|
2–3
|
Chelsea
|
A
|
ITL · UEFA Cup Winners' Cup
Quarter-final · Leg 2
|
| 13 Mar 1999 |
Chelsea
|
0–1
|
West Ham United
|
A
|
ENG · Premier League
|
| 10 Mar 1999 |
Chelsea
|
0–2
|
Manchester United
|
A
|
ENG · FA Cup
Round 6
|
| 07 Mar 1999 |
Manchester United
|
0–0
|
Chelsea
|
D
|
ENG · FA Cup
Round 6
|
| 04 Mar 1999 |
Chelsea
|
3–0
|
Vålerenga Fotball
|
H
|
ITL · UEFA Cup Winners' Cup
Quarter-final · Leg 1
|
| 27 Feb 1999 |
Chelsea
|
2–1
|
Liverpool
|
H
|
ENG · Premier League
|
| 20 Feb 1999 |
Nottingham Forest
|
1–3
|
Chelsea
|
A
|
ENG · Premier League
|
| 17 Feb 1999 |
Chelsea
|
1–1
|
Blackburn Rovers
|
D
|
ENG · Premier League
|
| 13 Feb 1999 |
Sheffield Wednesday
|
0–1
|
Chelsea
|
A
|
ENG · FA Cup
Round 5
|
