| Middlesbrough to Smolyan | 1,482.10 mi (2,385.21 km) |
| Middlesbrough to Sofia | 1,377.87 mi (2,217.47 km) |
| Middlesbrough to Sopot | 1,431.67 mi (2,304.06 km) |
| Middlesbrough to Sozopol | 1,551.84 mi (2,497.45 km) |
| Middlesbrough to Sredets | 1,536.31 mi (2,472.46 km) |
| Middlesbrough to Stamboliyski | 1,448.92 mi (2,331.81 km) |
| Middlesbrough to Stara Zagora | 1,475.02 mi (2,373.81 km) |
| Middlesbrough to Svilengrad | 1,527.38 mi (2,458.09 km) |
| Middlesbrough to Svishtov | 1,408.25 mi (2,266.36 km) |
| Middlesbrough to Targovishte | 1,471.24 mi (2,367.74 km) |
| Middlesbrough to Teteven | 1,401.25 mi (2,255.09 km) |
| Middlesbrough to Troyan | 1,419.28 mi (2,284.11 km) |
| Middlesbrough to Tryavna | 1,448.84 mi (2,331.69 km) |
| Middlesbrough to Tutrakan | 1,436.19 mi (2,311.33 km) |
| Middlesbrough to Varna | 1,523.02 mi (2,451.07 km) |
