| 29 Nov 1999 |
Olympiacos Piraeus
|
5–0
|
Ethnikos Asteras
|
H
|
GRE · Super League Greece
|
| 21 Nov 1999 |
Panathinaikos
|
2–0
|
Olympiacos Piraeus
|
H
|
GRE · Super League Greece
|
| 15 Nov 1999 |
AEK Athens
|
0–2
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 08 Nov 1999 |
Olympiacos Piraeus
|
4–1
|
PAOK Thessaloniki
|
H
|
GRE · Super League Greece
|
| 03 Nov 1999 |
Olympiacos Piraeus
|
1–0
|
Porto
|
H
|
ITL · UEFA Champions League
Group stage
|
| 26 Oct 1999 |
Real Madrid
|
3–0
|
Olympiacos Piraeus
|
H
|
ITL · UEFA Champions League
Group stage
|
| 23 Oct 1999 |
Olympiacos Piraeus
|
3–1
|
AO Trikala
|
H
|
GRE · Super League Greece
|
| 20 Oct 1999 |
Molde FK
|
3–2
|
Olympiacos Piraeus
|
H
|
ITL · UEFA Champions League
Group stage
|
| 15 Oct 1999 |
AO Kavala
|
0–5
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 13 Oct 1999 |
Olympiacos Piraeus
|
2–0
|
Apollon Krya Vrysi
|
H
|
GRE · Greek Football Cup
Group stage
|
| 04 Oct 1999 |
Juventus
|
1–2
|
Olympiacos Piraeus
|
A
|
ITL · UEFA Europa League
|
| 03 Oct 1999 |
Apollon Smyrnis
|
0–1
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 28 Sep 1999 |
Olympiacos Piraeus
|
3–1
|
Molde FK
|
H
|
ITL · UEFA Champions League
Group stage
|
| 25 Sep 1999 |
Olympiacos Piraeus
|
5–0
|
Panionios
|
H
|
GRE · Super League Greece
|
| 21 Sep 1999 |
Porto
|
2–0
|
Olympiacos Piraeus
|
H
|
ITL · UEFA Champions League
Group stage
|
| 20 Sep 1999 |
Olympiacos Piraeus
|
1–3
|
Juventus
|
A
|
ITL · UEFA Europa League
|
| 19 Sep 1999 |
Proodeftiki
|
0–3
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 15 Sep 1999 |
Olympiacos Piraeus
|
3–3
|
Real Madrid
|
D
|
ITL · UEFA Champions League
Group stage
|
| 08 Sep 1999 |
Edessaikos
|
0–2
|
Olympiacos Piraeus
|
A
|
GRE · Greek Football Cup
Group stage
|
| 29 Aug 1999 |
Olympiacos Piraeus
|
2–1
|
PAS Giannina
|
H
|
GRE · Greek Football Cup
Group stage
|
| 26 Aug 1999 |
Xanthi
|
1–5
|
Olympiacos Piraeus
|
A
|
GRE · Greek Football Cup
Group stage
|
| 11 Aug 1999 |
Olympiacos Piraeus
|
5–0
|
Naoussa
|
H
|
GRE · Greek Football Cup
Group stage
|
| 30 May 1999 |
Olympiacos Piraeus
|
0–0
|
AEK Athens
|
D
|
GRE · Super League Greece
|
| 23 May 1999 |
Panionios
|
1–4
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 19 May 1999 |
Xanthi
|
0–2
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 16 May 1999 |
Olympiacos Piraeus
|
3–2
|
Iraklis Thessaloniki
|
H
|
GRE · Super League Greece
|
| 12 May 1999 |
Ethnikos Piraeus
|
0–3
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 09 May 1999 |
Olympiacos Piraeus
|
0–0
|
Panathinaikos
|
D
|
GRE · Super League Greece
|
| 05 May 1999 |
Panathinaikos
|
0–2
|
Olympiacos Piraeus
|
A
|
GRE · Greek Football Cup
Final
|
| 02 May 1999 |
AO Kavala
|
0–2
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 25 Apr 1999 |
Olympiacos Piraeus
|
1–0
|
Aris Thessaloniki
|
H
|
GRE · Super League Greece
|
| 18 Apr 1999 |
Ionikos
|
1–3
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 11 Apr 1999 |
Iraklis Thessaloniki
|
1–1
|
Olympiacos Piraeus
|
D
|
GRE · Greek Football Cup
Semi-final
|
| 07 Apr 1999 |
Olympiacos Piraeus
|
4–0
|
Iraklis Thessaloniki
|
H
|
GRE · Greek Football Cup
Semi-final
|
| 04 Apr 1999 |
Olympiacos Piraeus
|
2–1
|
PAOK Thessaloniki
|
H
|
GRE · Super League Greece
|
| 22 Mar 1999 |
Olympiacos Piraeus
|
4–2
|
Ethnikos Asteras
|
H
|
GRE · Super League Greece
|
| 17 Mar 1999 |
Olympiacos Piraeus
|
1–1
|
Juventus
|
D
|
ITL · UEFA Champions League
Quarter-final · Leg 2
|
| 13 Mar 1999 |
Proodeftiki
|
0–1
|
Olympiacos Piraeus
|
A
|
GRE · Super League Greece
|
| 08 Mar 1999 |
Olympiacos Piraeus
|
3–0
|
Paniliakos
|
H
|
GRE · Super League Greece
|
| 03 Mar 1999 |
Juventus
|
2–1
|
Olympiacos Piraeus
|
H
|
ITL · UEFA Champions League
Quarter-final · Leg 1
|
