The city was incorporated in 1890 as "Middlesborough", named after the town of Middlesbrough on the south bank of the River Tees in North Yorkshire, England. However, the U.S. Post Office began using the spelling "Middlesboro" in 1894. Both spellings are used interchangeably; for example, the city's school district uses the Middlesboro spelling, as does the Kentucky Secretary of State's Land Office.
The city is located on the Kentucky side of the Cumberland Gap near the Cumberland Gap National Historical Park.
As the coal industry has declined over the last several years, the area has been increasingly hopeful for a growth in tourism, primarily from the nearby national park. The Pine Mountain State Resort Park is also located in nearby Pineville.
The town is home to the Middlesboro Country Club. Founded in 1889, the 9-hole course is one of the oldest golf courses in the country. The club also claims to be the oldest continuously played course in the nation. Pianist Ben Harney originated ragtime music in Middlesboro in the early 1890s, inspired by the fusion of African-American and local music styles heard in the community's saloons.
Geologists believe that the Middlesboro basin between Pine Mountain and the Cumberland Mountains is the remains of an ancient meteor crater, which would give the town the rare distinction of being one of the few cities in the world completely built inside a crater. The crater is one of three known astroblemes in the state.
It is the hometown of actor Lee Majors. Trish Suhr, comedian and star of The tv show "Clean House" was raised in Middlesboro. It is also the hometown of the late Susan Kingsley, stage and movie actress.
As of the census of 2000, there were 10,384 people, 4,443 households, and 2,927 families residing in the city. The population density was 1,359.1 people per square mile (524.8/km²). There were 4,955 housing units at an average density of 648.5/sq mi (250.4/km²). The racial makeup of the city was 92.84% White, 4.90% African American, 0.38% Native American, 0.63% Asian, 0.04% Pacific Islander, 0.19% from other races, and 1.02% from two or more races. Hispanic or Latino of any race were 0.79% of the population.
There were 4,443 households out of which 28.4% had children under the age of 18 living with them, 43.1% were married couples living together, 18.3% had a female householder with no husband present, and 34.1% were non-families. 31.5% of all households were made up of individuals and 14.2% had someone living alone who was 65 years of age or older. The average household size was 2.30 and the average family size was 2.88.
The age distribution is 23.6% under the age of 18, 8.9% from 18 to 24, 26.6% from 25 to 44, 23.9% from 45 to 64, and 17.0% who were 65 years of age or older. The median age was 39 years. For every 100 females there were 83.5 males. For every 100 females age 18 and over, there were 78.1 males.
The median income for a household in the city was $19,565, and the median income for a family was $25,016. Males had a median income of $23,285 versus $19,040 for females. The per capita income for the city was $13,189. About 24.4% of families and 28.1% of the population were below the poverty line, including 41.2% of those under age 18 and 16.5% of those age 65 or over.