It is the principal city of the Sikeston Micropolitan Statistical Area, which consists of all of Scott County, and has a total population of 41,143.

The area was claimed by the French as part of La Louisiane, and they ceded it in 1763 to the Spanish after being defeated by Britain in the Seven Years' War.

In April 1860, he had the city platted in anticipation of the completion of the Cairo and Fulton Railroad, which would intersect with the King's Highway.

Although Sikeston was a small village during the Civil War, its position at the railroad and highway intersection gave it strategic significance.

Around July 1861, Confederate forces of Brigadier General Gideon Johnson Pillow planned to link up with units commanded by Sterling Price and Benjamin McCulloch for an advance on St. Louis, using the Sikeston-area road of Kingshighway.

In preparation for this advance, Confederate General Jeff Thompson gathered Missouri state troops and irregulars near Sikeston; he robbed a bank in nearby Charleston to pay men and buy arms and supplies.

Legend has it that he hid part of his money in Sikeston under one of the oak trees at the corner of New Madrid Street and Kingshighway.

On October 4, Confederate General Jeff Thompson reached Sikeston, planning to strike Cape Girardeau; however, his manpower was limited, and he decided to retreat into the swamps off to the west.

On November 3, from Cairo, Illinois, US Brigadier General Ulysses S. Grant wrote a letter to Colonel Richard J. Oglesby, commander of the Union Headquarters District Southeast Missouri at Bird's Point, ordering his troops to "strike for Sikeston" from the Mississippi River town of Commerce.

Brigadier General Benjamin Prentiss and Colonel W. H. L. Wallace also converged in the Sikeston area in preparation of Grant's attack at the Battle of Belmont.

US Colonel William Pitt Kellogg, future governor of Louisiana, commanding the 7th Illinois cavalry, was the first to encounter the rebel sabotage of recently burned bridges and other obstructions.

Seeing that Colonel James Morgan's Illinois troops were reinforced by Brigadier General Schuyler Hamilton's 2nd Division, Thompson fled.

Entering the area from Bird's Point, Brigadier General Eleazor Arthur Paine, commander of the 4th Division of Army of the Mississippi, repaired the railroad and telegraph lines and used troops from Illinois to form a garrison for Sikeston, Bertrand, and Charleston.

On September 22, 1864, during Price's Raid, a Confederate force of 1,500 men near Sikeston, under the command of Colonel William Lafayette Jeffers, attacked Captain Lewis Sells' company of Union soldiers who were moving from Cape Girardeau to reinforce two companies of soldiers in Bloomfield.

[7] One of the first rail lines west of the Mississippi River ran to Sikeston, and it was the terminus of the Cairo and Fulton Railroad until 1872.

Prominent individuals who stayed at this hotel included Harry S. Truman, Alben W. Barkley, and Tom Pendergast.

Long barrack-style buildings were constructed to hold the Missouri Institute of Aeronautics, established after General Hap Arnold asked flight training operations to triple their enrollments.

In June 1940, a home at West Gladys and New Madrid streets was transformed into a district infirmary in coordination with the building of the new air barracks.

[10] World War II flying aces Robert S. Johnson and Harold E. Comstock trained at this location.

During World War II, local National Guard unit Company K was assigned to the Western Defense Command in California.

In the early hours of Sunday, January 25, 1942, a Black man named Cleo Wright was arrested on charges of allegedly assaulting a white woman.

In 2000, the remains of Mason Yarbrough, a Sikeston native and World War II marine, were found in the Pacific area on Makin Island and returned to his hometown for a military funeral.

In the 1920s, the Little River Drainage District was formed to drain the low land area west of the Sikeston Ridge.

[11] On May 15, 1986, a tornado hit the city of Sikeston and destroyed about 100 homes, prompting Governor John Ashcroft to visit and call on the National Guard for assistance.

On the same day, the nearby community of Vanduser was also hit by a tornado while storms precipitated flooding to the north in Cape Girardeau.

Restoration of city electrical power was delayed as a circuit breaker at the Coleman Substation had exploded on January 21 just before the ice storm hit.

Governor Jay Nixon surveyed the fog-covered damage by helicopter and visited the Sikeston Field House which was being used as a shelter.

The largest park, the Sikeston Recreation Complex, features a fishing lake, picnic shelters and playground equipment.

The parade, one of the largest in Missouri, featured floats, area marching bands, and state and national politicians.

[2] Of all residents in Sikeston who are 25 years of age and older, 73.3% hold a high school diploma or higher as their highest educational attainment; 14.2% possess a bachelor's degree or higher; 5.0% hold a graduate or professional degree; and 26.7% have less than a high school diploma.