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Competition:
All rounds were played in one game elimination format.
Clubs:
The Cup was played by 64 clubs.
Qualification:
1. Lig: 18
- 15 - Top 15 clubs of 1998-1999 1. Lig (R3)
- 3 - Clubs promoted from 1998-1999 2.Lig (R2)
2. Lig: 38 - 2
- 3 - Relegated clubs from 1998-1999 1. Lig (R3)
- 7 - 7 clubs which didn't promote from 1998-1999 2. Lig Promotion group (R2)
- 20 - Top 4 clubs from 1998-1999 2. Lig Classification groups (R1)
- 8 - Clubs promoted from 1998-1999 3.Lig
3. Lig: 8 - 3
- 8 - Clubs ranked top 2 at 1998-1999 3. Lig groups, but didn't get promotion. (R1) - Darıca Gençlerbirliği and Düzcespor withdrew because of the Marmara earthquake and Mardinspor was penalized. Third clubs in their groups were admitted to replace them.
Final
 Galatasaray İstanbul
03.05 Galatasaray İST 5-3 ANT Antalyaspor aet. Reg score: 2-2
FINAL
03/05/2000 15:00 Atatürk Stadyumu, Diyarbakır - Metin Tokat, Turgay Güdü, Cengiz Akyüz
Galatasaray 5-3 Antalyaspor - aet
1-0 Ümit Davala 13, 1-1 Mustafa Gürsel 40. 1-2 Zafer Demiray 70, 2-2 Márcio Mixirica 72. 2-3 Kamil Çakır 94, 3-3 Hakan Ünsal 99. 4-3 Mehmet Yozgatlı 112, 5-3 Hakan Şükür 113
Galatasaray Kerem İnan, Carlos Alberto de Oliveria "Capone", Gheorghe Popescu (Mehmet Yozgatlı 97), Ahmet Yıldırım, Ergün Penbe, Ümit Davala, Okan Buruk, Gheorghe Hagi (Hasan Şaş 90), Hakan Ünsal "K.Hakan", Hakan Şükür "B.Hakan", Arif Erdem (Márcio Mandinga dos Santos "Márcio Mixirica" 46)
Coach: Fatih Terim
 Márcio Mixirica 73, Gheorghe Hagi 74
Antalyaspor Adnan Karahan, Nuri Kamburoğlu, Gocho Petkov Guintchev, Kamil Çakır, Fazlı Ulusal (Mame Adama Guèye 64), Burhan Saatçioğlu, Mustafa Gürsel, Vedin Musić, Dursun Karaman (Maurizio Guadino 68), Şenol Yavaş (Ahmet Sönmez 91), Zafer Demiray
Coach: Metin Ünal
Kamil Çakır 58, Mustafa Gürsel 72
Galatasaray won the cup with a 5-3 score
Semi Finals
16.02 MKE Ankaragücü ANK 0-2 İST Galatasaray
16.02 Antalyaspor ANT 2-0 BUR Bursaspor
Quarter Finals
02.02 MKE Ankaragücü ANK 7-0 AYD Yeni Nazillispor 2
02.02 Antalyaspor ANT 3-1 ÇAN Çanakkale Dardanel 2
02.02 Bursaspor BUR 1-0 GAZ Gaziantepspor
02.02 Trabzonspor TRA 1-2 İST Galatasaray
Round 4
8 of 16 clubs progressed to Quarter Finals.
19.01 Yeni Nazillispor 2 AYD 0-0 ERZ Erzurumspor pen: 5-4
18.01 Bursaspor BUR 3-0 VAN Vanspor
18.01 Çanakkale Dardanel 2 ÇAN 2-0 İST Pendik 2
19.01 Gaziantepspor GAZ 4-3 İZM Altay aet. reg score: 1-1
19.01 Bakırköy 2 İST 0-2 ANT Antalyaspor
19.01 Galatasaray İST 2-1 SAM Samsunspor
19.01 İstanbulspor İST 1-2 ANK MKE Ankaragücü
19.01 Kocaelispor KOC 0-2 TRA Trabzonspor
Round 3
16 of 32 clubs progressed to Round 4.
14.12 Adanaspor ADA 1-2 SAM Samsunspor
15.12 Antalyaspor ANT 2-0 YOZ Yimpaş Yozgatspor 2
15.12 Yeni Nazillispor 2 AYD 1-1 ANK Gençlerbirliği pen: 4-1 reg score: 1-1
15.12 Çanakkale Dardanel 2 ÇAN 1-0 İST Beşiktaş
15.12 Elazığspor 2 ELA 0-5 GAZ Gaziantepspor
15.12 Erzurumspor ERZ 4-1 DEN Denizlispor
15.12 Bakırköy 2 İST 3-0 SAK Sakaryaspor 2 awd *
15.12 Galatasaray İST 5-1 ANK BB Ankaraspor
15.12 İstanbulspor İST 2-0 KON Konya SÜ Endüstrispor 2
14.12 Pendik 2 İST 2-1 İST Fenerbahçe
15.12 Kayserispor 2 KAY 1-2 BUR Bursaspor
15.12 KDÇ Karabükspor 2 KRB 0-4 KOC Kocaelispor
15.12 Çaykur Rizespor 2 RİZ 2-2 ANK MKE Ankaragücü pen: 3-4 reg score: 2-2
15.12 Siirt Jet-Pa 2 Sİİ 1-1 İZM Altay pen: 1-4 reg score: 1-1
15.12 Trabzonspor TRA 3-1 İZM Göztepe
15.12 Vanspor VAN 1-0 İST Kartal 2
* - Sakaryaspor withdrew because of Marmara earthquake
Round 2
14 of 28 clubs progressed to Round 3.
10.11 BB Ankaraspor 2 ANK 3-2 MER Mersin İdman Yurdu 2
10.11 Yeni Nazillispor 2 AYD 5-2 AYD Aydınspor 2
10.11 Bakırköy 2 İST 1-1 İST Zeytinburnu 2 pen: 3-1 reg score: 1-1
10.11 Kartal 2 İST 1-0 İST İstanbul BB 2
10.11 Sarıyer 2 İST 1-2 İST Pendik 2
10.11 Aliağa Petkimspor 3 İZM 0-4 DEN Denizlispor
10.11 Göztepe İZM 3-2 MUĞ Marmarisspor 2
10.11 Kayserispor 2 KAY 1-0 KIR MKE Kırıkkalespor 2
10.11 Konya SÜ Endüstrispor 2 KON 3-0 İZM Bucaspor 2
10.11 Malatya Belediye 2 MAL 1-1 ELA Elazığspor 2 pen: 1-3 reg score: 1-1
10.11 Çaykur Rizespor 2 RİZ 5-0 ART Artvin Hopaspor 2
10.11 Siirt Jet-Pa 2 Sİİ 5-2 ŞAN Şanlıurfaspor 2
10.11 Vanspor VAN 4-2 DİY Diyarbakırspor 2
10.11 Yimpaş Yozgatspor 2 YOZ 3-1 ANK Şekerspor 2
Round 1
18 of 36 clubs progressed to Round 2.
27.10 Ceyhanspor 3 ADA 0-1 MER Mersin İdman Yurdu 2
27.10 Ankara ASAŞ 2 ANK 1-2 ANK BB Ankaraspor 2
27.10 Doğubayazıtspor 3 AĞR 1-2 ŞAN Şanlıurfaspor 2
27.10 Artvin Hopaspor 2 ART 3-2 AMA Amasyaspor 2 in Artvin
27.10 Yeni Nazillispor 2 AYD 3-1 AYD Kuşadasıspor 2
27.10 Diyarbakırspor 2 DİY 2-0 BAT Batman Petrolspor 2
27.10 Hakkarispor 3 HAK 1-2 MAL Malatya Belediye 2
27.10 Beylerbeyi 3 İST 1-3 İST Zeytinburnu 2
27.10 Eyüpspor 3 İST 2-5 İST Bakırköy 2
27.10 Gaziosmanpaşa 2 İST 2-4 İST Pendik 2
27.10 Kartal 2 İST 1-0 KOC Gebzespor 3
27.10 Aliağa Petkimspor 3 İZM 2-0 İZM İzmirspor 2
27.10 Bucaspor 2 İZM 1-0 BİL Bilecikspor 3
27.10 MKE Kırıkkalespor 2 KIR 1-0 BOL Boluspor 2
27.10 Konya SÜ Endüstrispor 2 KON 1-0 GAZ Gaziantep BB 2
27.10 Marmarisspor 2 MUĞ 4-2 İZM Karşıyaka 2
27.10 Siirt Jet-Pa 2 Sİİ 2-0 ADI Adıyamanspor 2
27.10 Yimpaş Yozgatspor 2 YOZ 3-1 SİV Sivasspor 2
The Champ - Galatasaray
G W D L F A
Galatasaray 5 5 0 0 16 6
Trainer: Fatih Terim
Goalies: Claudio Taffarel (3), Kerem İnan (1), Mehmet Bölükbaşı (1)
Defense: Ümit Davala (5,2), Carlos Alberto de Oliveria "Capone" (4,1), Bülent Korkmaz (3,1), Gheorghe Popescu (3),
Fatih Akyel (2), Ahmet Yıldırım (1), Hakan Ünsal "K.Hakan" (1,1)
Midfield: Hasan Şaş (5,1), Okan Buruk (5,1), Emre Belözoğlu (4), Suat Kaya (4), Ergün Penbe (3), Sergen Yalçın (3,2),
Tugay Kerimoğlu (1), Ceyhun Müderrisoğlu (1), Emrah Eren (1), Gürol Azer (1)
Forwards: Márcio Mandinga dos Santos "Márcio Mixirica" (5,3), Arif Erdem (3), Hakan Şükür "B.Hakan" (3,1),
Gheorghe Hagi (3,1), Mehmet Yozgatlı (2,1), Saffet Akyüz (1,1)
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1999-2000 - 38. Türkiye Kupası