Major General Sterling Price commanded the expedition, and initially hoped to capture St. Louis.

After the strength of the Union garrison at Jefferson City convinced Price to cancel a planned attempt to capture the place, he led his army into the pro-Confederate region of Little Dixie, where recruiting efforts were successful.

Learning of a Union weapons cache at Glasgow, Price sent Brigadier General John B. Clark Jr. with two brigades on a side raid to capture it.

The Union garrison of Glasgow was commanded by Colonel Chester Harding Jr., and was mostly composed of militia and men of the 43rd Missouri Infantry Regiment.

After the Union commander rejected a surrender offer from Clark, the main attack began at about 08:00; it occurred late due to delays in reaching Glasgow.

Harding's men were driven back into the town and burned 50,000 rations to prevent them from falling into Confederate hands.

Clark's men paroled the Union soldiers, captured 1,000 uniform overcoats and 1,200 weapons, and burned a steamboat.

[5] As events east of the Mississippi River turned against the Confederates, General Edmund Kirby Smith, Confederate commander of the Trans-Mississippi Department, was ordered to transfer the infantry under his command to the fighting further east, but this was not possible due to the Union Navy's control of the Mississippi River.

[12] In late September, the Confederates encountered a small Union force holding Fort Davidson near the town of Pilot Knob.

[13] Parts of the Confederate army advanced as far as Franklin, but then turned westwards to Jefferson City via Union and Washington.

[14] Price had abandoned intentions to attack St. Louis[14] due to the defeat at Pilot Knob[15] and was not making a serious attempt to capture the city in the advance to Franklin.

[19] Price determined that Jefferson City was too strong to attack, and continued moving westwards along the course of the Missouri River.

Boonville was part of a pro-Confederate area known as Little Dixie, and many men, including Bloody Bill Anderson and his guerrillas, joined the Confederates.

[21][b] Union troops followed Price westwards; one body was to the east of Boonville at Rocheport, and another, under Brigadier General John B. Sanborn, was to the south at California.

[22] On the 11th, Sanborn moved north and skirmished with the Confederates, who abandoned Boonville the next day and continued west in the direction of Marshall.

Late on October 12, Price learned of rumors that a substantial store of weapons was held by the Union garrison of Glasgow, across the Missouri River and 20 miles (32 km) north of Boonville.

One, under Brigadier General[d] M. Jeff Thompson, commander of Shelby's Iron Brigade, was sent 26 miles (42 km) south of Price's camp to Sedalia, which it captured on October 15.

After hearing rumors that the garrison of Glasgow had a "tin-clad boat", Clark asked Price for more artillery.

One of the ships, Benton, returned to Jefferson City, while the other, West Wind, stayed at Glasgow,[36] as its draft was expected to be too deep for the falling water levels on the river.

[41] Elements of the 43rd Missouri Infantry held east and west positions south of town on the external line, near where the roads crossed Greggs Creek.

[37] At around 05:00 on October 15, Collins's Battery opened fire, aiming primarily for West Wind, visible campfires, and exposed streets in the town.

[41][43] Clark's force, delayed an hour while trying to cross the Missouri River,[44] arrived later than Shelby expected.

[46] Clarks' main body south of town forced its way across Greggs Creek beginning around 08:00, although the Union defenders put up a hardy fight.

The Confederates reached West Wind but found the steamboat's engines had been rendered nonfunctional, and they had to return to Shelby.

Before surrendering, Union troops burned 50,000 rations in Glasgow's City Hall to prevent them from falling into Confederate hands.

[51] Preservationist Frances E. Kennedy places the number of paroled Union soldiers as over 600, not counting battle losses.

[55] An engine removed from the riverbed at Glasgow during a World War II scrap drive was rumored to have come from the vessel.