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Competition:
The first two rounds were played in a one-legged knock out format with extra time and penalty shoout-out. The rest of the competition was two-legged knock out format. If the aggregate score was tied, the goal scored away counted double. Extra time and penalty-shoot-out were also in use to break further ties.
Clubs:
The Cup was played by 71 clubs.
Qualification:
1. Lig: 19
- 19 - 1. Lig clubs (R3)
2. Ligi: 34 - 2
- 4 - Relegated clubs from 1987-1988 1. Lig (R1)
- 21 - Clubs finishing 2nd through 8th at three 1987-1988 2. Lig groups (R1)
- 9 - Promoted clubs from 1987-1988 3. Lig (R1)
3. Lig: 17 - 3
- 17 - Clubs finishing at 2nd in Group 1 and top 3 in other eight groups of 1987-1988 3. Lig (R1)
Amateurs: 1 - A
- 1 - Beşiktaş, 1987-1988 Turkish Amateur Champion (R1)
Final
 Beşiktaş İstanbul
25.05 21.06 Beşiktaş İST 2-1 1-0 İST Fenerbahçe
21/06/1989 17:00 Fenerbahçe Stadyumu, İstanbul - Özcan Oal, Taner Yalçındağ, Argun Darıcı
Fenerbahçe 0-1 Beşiktaş
0-1 Leslie "Les" Ferdinand 15
Fenerbahçe Toni Schumacher, İsmail Kartal, Nezihi Tosuncuk, Müjdat Yetkiner, Şenol Ustaömer "K.Şenol", Turhan Sofuoğlu (Ergin Parlar 63), Oğuz Çetin, Serdar Şenkaya (Bilal Şar 63), Rıdvan Dilmen, Hasan Vezir, Aykut Kocaman
Coach: Todor Veselinović (YUG)
 Nezihi Tosuncuk, İsmail Kartal, Ergin Parlar
Beşiktaş Rade Zalad, Recep Çetin, Gökhan Keskin, Ulvi Güveneroğlu, Kadir Akbulut, Metin Tekin (Feyyaz Uçar 77), Zeki Önatlı (Şenol Fidan 51), Rıza Çalımbay, Mehmet Özdilek, Ali Gültiken, Leslie "Les" Ferdinand
Coach: Gordon Milne (ENG)
Kadir Akbulut, Mehmet Özdilek
25/05/1989 16:30 İnönü Stadyumu, İstanbul - İhsan Türe, Hüseyin Su, Ahmet Erdoğan
Beşiktaş 2-1 Fenerbahçe
0-1 Oğuz Çetin 46, 1-1 Ali Gültiken 76, 2-1 Feyyaz Uçar 86
Beşiktaş Rade Zalad, Recep Çetin, Gökhan Keskin, Ulvi Güveneroğlu, Bünyamin Süral, Mehmet Özdilek, Rıza Çalımbay, Şenol Fidan, Metin Tekin (Ali Gültiken 73), Leslie "Les" Ferdinand, Feyyaz Uçar
Coach: Gordon Milne (ENG)
Bünyamin Süral, Gökhan Keskin, Leslie "Les" Ferdinand
Fenerbahçe Toni Schumacher, İsmail Kartal, Nezihi Tosuncuk, Müjdat Yetkiner, Şenol Ustaömer "K.Şenol", Turhan Sofuoğlu, Serdar Şenkaya (Taygun Erdem 79), Oğuz Çetin, Hakan Tecimer (Bilal Şar 62), Rıdvan Dilmen, Aykut Kocaman
Coach: Todor Veselinović (YUG)
İsmail Kartal, Nezihi Tosuncuk
Beşiktaş won the cup with a 3-1 aggregate score
Semi Finals
07.06 18.06 Fenerbahçe İST 1-0 1-2 MAL Malatyaspor
07.06 18.06 Konyaspor KON 1-2 1-3 İST Beşiktaş
Malatyaspor was penalized with one game without spectators penalty because of the incidents
at 2nd leg, but it was changed to one game venue closing after their appeal
Quarter Finals
22.03 03.05 Fenerbahçe İST 2-2 4-3 İST Galatasaray
22.03 03.05 Karşıyaka İZM 0-3 0-1 İST Beşiktaş
22.03 03.05 Konyaspor KON 0-0 3-2 İST Sarıyer
22.03 03.05 Malatyaspor MAL 2-0 3-1 İST Bakırköy 2
Round 4
8 of 16 clubs progressed to Quarter Finals.
08.02 15.02 Adanaspor ADA 1-0 0-2 İST Bakırköy 2
08.02 15.02 Bursaspor BUR 0-1 2-4 İST Galatasaray
08.02 15.02 Beşiktaş İST 2-1 2-0 KOC Kocaelispor 2
08.02 15.02 Sarıyer İST 0-0 1-1 BOL Boluspor
08.02 15.02 Karşıyaka İZM 4-1 3-2 ANK MKE Ankaragücü
08.02 15.02 Konyaspor KON 2-3 4-2 ESK Eskişehirspor
08.02 15.02 Malatyaspor MAL 1-0 2-0 ADA Adana Demirspor
08.02 15.02 Trabzonspor TRA 1-0 1-3 İST Fenerbahçe aet
Round 3
16 of 32 clubs progressed to Round 4.
25.01 01.02 Adana Demirspor ADA 4-0 2-1 KON Etibank Seydişehir Aliminyumspor 3
25.01 01.02 Adanaspor ADA 4-1 3-0 RİZ Rizespor
25.01 01.02 Ayvalıkgücü 2 BAL 0-1 1-5 İST Galatasaray
25.01 01.02 Boluspor BOL 3-1 3-1 ANK PTT
25.01 01.02 Bursaspor II 2 BUR 1-2 2-3 ANK MKE Ankaragücü
26.01 01.02 Beşiktaş İST 4-0 5-1 İST Beşiktaş a
25.01 01.02 Fenerbahçe İST 5-1 1-0 AYD Kuşadasıspor 2
25.01 01.02 Altay İZM 2-3 2-1 KOC Kocaelispor 2
25.01 01.02 Kahramanmaraşspor KAH 1-2 1-1 BUR Bursaspor
25.01 01.02 Kayserispor 2 KAY 0-1 1-2 ESK Eskişehirspor (2) in Ankara
25.01 01.02 Tavşanlı Linyitspor 3 KÜT 0-4 0-2 İST Sarıyer
25.01 01.02 Malatyaspor MAL 0-0 2-0 ANK Ankara Demirspor 3
25.01 01.02 Sakaryaspor SAK 2-1 0-3 TRA Trabzonspor
25.01 01.02 Çarşambaspor 2 SAM 0-1 0-2 İZM Karşıyaka
25.01 01.02 Samsunspor SAM 0-3 0-3 İST Bakırköy 2 both games awarded
25.01 01.02 Siirt Köy Hizmetleri YSE 2 Sİİ 1-1 1-2 KON Konyaspor
Samsunspor had a deadly traffic accident and were excused from the competition
Round 2
13 of 26 clubs progressed to Round 3.
07.12 Petrol Ofisi 2 ANK 1-3 ANK Ankara Demirspor 3
07.12 PTT 2 ANK 1-0 ANK Gençlerbirliği 2
07.12 Kuşadasıspor 2 AYD 4-0 AYD Aydınspor 2
07.12 Ayvalıkgücü 2 BAL 2-1 EDİ Uzunköprüspor 2
07.12 Bursaspor II 2 BUR 4-2 BUR İnegölspor 2 reg time: 2-2
07.12 Elazığspor 3 ELA 1-1 Sİİ Siirt Köy Hizmetleri YSE 2 penalties: 3-4 reg time: 1-1
07.12 Bakırköy 2 İST 6-4 İST Kartal 2 reg time: 4-4
07.12 Beşiktaş A İST 4-4 İST Zeytinburnu 2 penalties: 4-2 reg time: 3-3
07.12 Kayserispor 2 KAY 2-1 GAZ Gaziantepspor 2
07.12 Kocaelispor 2 KOC 3-1 ZON Erdemir Ereğlispor 3
07.12 Etibank Seydişehir Aliminyumspor 3 KON 6-2 ANT Antalyaspor 2
07.12 Yeni Salihlispor 2 MAN 1-2 KÜT Tavşanlı Linyitspor 3 reg time: 1-1
07.12 Çarşambaspor 2 SAM 2-0 ERZ Erzurumspor 2
Round 1
26 of 52 clubs progressed to Round 2.
17.11 Ankara Demirspor 3 ANK 1-0 ANK Polatlıspor 2
16.11 Gençlerbirliği 2 ANK 5-1 ÇOR Çorumspor 3
17.11 Petrol Ofisi 2 ANK 3-2 NEV Nevşehirspor 2
16.11 PTT 2 ANK 3-0 SAM Bafraspor 3
16.11 Antalyaspor 2 ANT 5-2 DEN Denizlispor 2
16.11 Aydınspor 2 AYD 3-1 İZM Altınordu 2
16.11 Kuşadasıspor 2 AYD 2-0 İZM Göztepe 2
16.11 Batman Petrolspor 3 BAT 0-1 ELA Elazığspor 3
16.11 Bursaspor II 2 BUR 3-0 BAL Gönenspor 3
16.11 Sönmez Filament 2 BUR 1-2 BUR İnegölspor 2
16.11 Uzunköprüspor 2 EDİ 0-0 ÇAN Bigaspor 3 penalties: 5-4
23.11 Erzurumspor 2 ERZ 5-1 ORD Orduspor 2
16.11 Hatayspor 3 HAT 0-1 GAZ Gaziantepspor 2
16.11 Bakırköy 2 İST 8-0 İST Vefa 3
16.11 Beşiktaş A İST 3-0 İST Bayrampaşa 3
16.11 Kartal 2 İST 3-2 İST Sümerbank Beykoz 2
16.11 Zeytinburnu 2 İST 6-4 İST Gaziosmanpaşa 3 aet. reg time: 3-3
16.11 Kayserispor 2 KAY 2-1 KAH Elbistanspor 3
16.11 Kocaelispor 2 KOC 3-1 ZON Zonguldakspor 2
16.11 Etibank Seydişehir Aliminyumspor 3 KON 2-1 ANT Alanyaspor 2
16.11 Kütahyaspor 2 KÜT 1-2 KÜT Tavşanlı Linyitspor 3
16.11 Yeni Salihlispor 2 MAN 3-2 MAN Yeni Turgutluspor 3
16.11 Mardinspor 2 MAR 0-1 Sİİ Siirt Köy Hizmetleri YSE 2
16.11 Çarşambaspor 2 SAM 1-0 GİR Giresunspor 2
16.11 Tekirdağspor 3 TEK 1-2 BAL Ayvalıkgücü 2
16.11 Erdemir Ereğlispor 3 ZON 0-0 KRB DÇ Karabükspor 2 penalties: 4-3
The Champ - Beşiktaş
G W D L F A
Beşiktaş 10 10 0 0 25 5
Trainer: Gordon Milne
Goalies: Rade Zalad (9), Metin Akçevre (1)
Defense: Recep Çetin (9), Ulvi Güveneroğlu (9,1), Gökhan Keskin (8,1), Kadir Akbulut (8,1), Bünyamin Süral (3),
Turan Uzun (3), İsmail Taviş (2)
Midfield: Mehmet Özdilek (10,1), Rıza Çalımbay (9,1), Zeki Önatlı (9), Şenol Fidan (8), Halim Okta (3,2), Cem Kumbasar (1)
Forwards: Metin Tekin "B.Metin" (9,3), Ali Gültiken (9,8), Feyyaz Uçar (9,3), Leslie "Les" Ferdinand (5,4)
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1988-1989 - 27. Federasyon Kupası