| Datum | Spieler | Von | Zu | Zahlung / Abrechnung | Dauer | |
| 06.08.2019 12:28 | Abdullah Abuayman | Jokerit Vaasa | Middlesbrough | 233.379 | Euro | 36 ZATs |
| 07.07.2019 20:45 | Fabio Femia | AK Lustenau | Middlesbrough | 236.063 | Euro | 36 ZATs |
| 28.05.2018 08:58 | Jesus Antón | CD Mataro | Middlesbrough | 125.442 | Euro | 36 ZATs |
| 17.05.2018 08:44 | Mihal Ramadani | Armentieres FC | Middlesbrough | 187.295 | Euro | 36 ZATs |
| 03.02.2017 23:27 | Burt Woodrow | Beira-Mar | Middlesbrough | 259.043 | Euro | 66 ZATs |
| 10.01.2017 20:53 | Bernardo Belmondo | KC Waregem | Middlesbrough | 241.205 | Euro | 72 ZATs |
| 02.06.2016 09:29 | Aleksandar Stojkovic | Drovno Siroki Brijeg | Middlesbrough | 159.386 | Euro | 96 ZATs |
| 30.05.2016 12:28 | Pakal Beliajeva | Sparta Zizkov | Middlesbrough | 179.669 | Euro | 48 ZATs |
| 29.05.2016 14:26 | Filip Djokic | Drovno Siroki Brijeg | Middlesbrough | 266.924 | Euro | 48 ZATs |
| 22.12.2015 12:46 | Sönke Meskath | 1911 Baunatal | Middlesbrough | 444.538 | Euro | 36 ZATs |
| 22.12.2015 12:41 | Pakal Beliajeva | Sparta Zizkov | Middlesbrough | 255.098 | Euro | 36 ZATs |
| 21.12.2015 23:01 | Talgat Musatayev | Ballycastle Rangers | Middlesbrough | 262.598 | Euro | 36 ZATs |