| Season: | 1999–2000 |
| Nextseason: | 2000–01 |
1999–2000 Trabzonspor season was the 25th consecutive season that the club played in the 1. Lig.
Trabzonspor finished 6th the 1999–2000 season. Trabzonspor was included in the Turkish Cup from 3rd round. Galatasaray defeated Trabzonspor 2 – 1 in Trabzon in quarter finals. Trabzonspor could not qualify to play in any European cup games for the 1999–2000 season.
| Pos. | Player | Transferred from | Transfer type | Fee | Date | Ref. | ||
|---|---|---|---|---|---|---|---|---|
| 1 | - |  Abdülkadir Demirci | Gaziantepspor | Transfer | - | 6 July 1999 | ||
| 2 | FW | Bülent Uygun | Çanakkale Dardanelspor | Transfer | - | 29 July 1999 | ||
| 3 | - | Cem Beceren | Gaziantepspor | Transfer | - | 6 July 1999 | ||
| 4 | - |  Emmanuel Tetteh | Vanspor | Transfer | - | 30 November 1999 | ||
| 5 | - | Erman Özgür | Çanakkale Dardanelspor | Transfer | - | 6 July 1999 | ||
| 6 | - | Erol Bulut | Fenerbahçe | Transfer | - | 10 Aralık 1999 | ||
| 7 | - | Hami Mandıralı | FC Schalke 04 | Transfer | - | 12 July 1999 | ||
| 8 | - | Hüseyin Çimşir | Sakaryaspor | Was hired. Returned. | - | - | ||
| 9 | - |   Igor Sasa Nikolovski | Sakaryaspor | Transfer | - | 7 July 1999 | ||
| 10 | - | Murat Bölükbaş | Fenerbahçe | Transfer | - | 16 June 1999 | ||
| 11 | - | Nesim Özgür | İstanbulspor | Transfer | - | 20 July 1999 | ||
| 12 | FW |  Rogério Oliveira da Costa | FK Pobeda | Transfer | - | - | ||
| 13 | - | Tamer Tuna | Çanakkale Dardanelspor | Transfer | - | 12 July 1999 | ||
| 14 | - | Ufuk Ali | Trabzonspor (youth team) | Professional debut | - | 30 July 1999 | ||
| 15 | - | Yusuf Tokaç | Beşiktaş | Transfer | - | 9 July 1999 |
| Pos. | Player | Transferred to | Transfer type | Fee | Date | Ref. | ||
|---|---|---|---|---|---|---|---|---|
| 1 | DF | Abdullah Ercan | Fenerbahçe | Transfer | - | 7 June 1999 | ||
| 2 | - | Ahmet Yılmazer | Akçaabat Sebatspor | Transfer | - | 13 August 1999 | ||
| 3 | - | Birol Güneş | Eskişehirspor | Transfer | - | 1 September 1999 | ||
| 4 | FW | Çetin Güner | FC Basel | Loan | - | - | ||
| 5 | - | Dilaver Satılmış | FC Luzern | Transfer | - | - | ||
| 6 | - | Erdal Eraşkın | - | - | - | - | ||
| 7 | - | Feti Okuroğlu | İzmirspor | Transfer | - | - | ||
| 8 | - | Gökhan Kolomoç | Mersin İdman Yurdu | Loan | - | 21 October 1999 | ||
| 9 | - |  Karel Rada | SK Slavia Prague | Transfer | - | - | ||
| 10 | FW | Kevin Campbell | Everton F.C. | Transfer | - | - | ||
| 11 | - | Mehmet Zengin | Çanakkale Dardanelspor | Transfer | - | 5 August 1999 | ||
| 12 | - | Ogün Temizkanoğlu | Fenerbahçe | Transfer | - | 8 June 1999 | ||
| 13 | DF | Recep Çetin | İstanbulspor | Transfer | - | 21 December 1999 | ||
| 14 | - | Seyit Cem Ünsal | Vanspor | Loan | - | 14 January 2000 | ||
| 15 | MF | Ünal Karaman | Ankaragücü | Transfer | - | 29 July 1999 | ||
| 16 | FW |  Yuriy Kalitvintsev | FC Arsenal Kyiv | Transfer | - | - |
| Player | 1 .Lig | Turkish Cup | Total | |
|---|---|---|---|---|
| 1 | Hami Mandıralı | 13 | 3 | 16 |
| 2 | Abdülkadir Demirci | 9 | - | 9 |
| 3 | Davor Vugrinec | 5 | 2 | 7 |
| 4 | Osman Özköylü | 4 | - | 4 |
| 5 | Erman Özgür | 3 | - | 3 |
| Orhan Çıkırıkçı | 2 | 1 | 3 | |
| Tamer Tuna | 3 | - | 3 | |
| 8 | Fatih Tekke | 2 | - | 2 |
| Murat Bölükbaş | 2 | - | 2 | |
| 10 | Nesim Özgür | 1 | - | 1 |
| Rogério Oliveira da Costa | 1 | - | 1 | |
| Selahattin Kınalı | 1 | - | 1 |
Trabzonspor couldn't qualify to play in any European cup games in 1999–2000 season.