| Southborough to Oswego (Illinois) | 4,009.83 mi (6,453.19 km) |
| Southborough to Oswego (New York) | 3,469.51 mi (5,583.64 km) |
| Southborough to Otsego (Minnesota) | 4,037.74 mi (6,498.12 km) |
| Southborough to Ottawa (Illinois) | 4,043.78 mi (6,507.83 km) |
| Southborough to Ottawa (Kansas) | 4,420.47 mi (7,114.06 km) |
| Southborough to Ottumwa (Iowa) | 4,195.49 mi (6,751.98 km) |
| Southborough to Overland (Missouri) | 4,229.44 mi (6,806.63 km) |
| Southborough to Overland Park (Kansas) | 4,384.58 mi (7,056.30 km) |
| Southborough to Overlea (Maryland) | 3,646.75 mi (5,868.87 km) |
| Southborough to Oviedo (Florida) | 4,346.88 mi (6,995.63 km) |
| Southborough to Owasso (Oklahoma) | 4,557.72 mi (7,334.95 km) |
| Southborough to Owatonna (Minnesota) | 4,079.04 mi (6,564.58 km) |
| Southborough to Owensboro (Kentucky) | 4,147.52 mi (6,674.78 km) |
| Southborough to Owings Mills (Maryland) | 3,655.85 mi (5,883.53 km) |
| Southborough to Owosso (Michigan) | 3,790.36 mi (6,100.00 km) |
