This is from the post I did right before your query:
The units raised by Thomas Woodward underwent some changes and designations during the war. This is from research that I have done to determine what command assisted in the retaking of Clarksville, TN in August, 1862. It is based on the KY Adjutant General's Records and the CSRs for Woodward's units. As follows:
For Thomas G. Woodward - born July 30, 1827, New Haven, CT. Attended Yale and West Point but was dismissed from both due to drunkenness. Moved to Christian County, KY 1846-1847. Became a teacher and lawyer.
On April 9, 1861 he raised the Oak Grove Rangers, a one year command, who were accepted into Tennessee service on June 25th at Camp Trousdale in Sumner County. The unit grew so large that when merged into the 1st Kentucky Cavalry (Helm's - 1st organization), it became Companies A and B of that regiment. According to the KY Adjutant General Records, Co. A joined the 1st KY Cavalry on October 5, 1861. It's captain was Darwin Bell. The men came from Russellville, Bowling Green and a number of Tennessee men. Co. B was led by Capt. Jack Jones then George Beckley. They joined the regiment on October 14th, 1861 and also had a lot of Tennesseans in the command.
Woodward was promoted to Lt. Colonel in December, 1861 and to colonel on March 14, 1862.
The 1st Kentucky Cavalry (Helm's) was reorganized on September 1, 1862. Only two of its companies were enlisted for more than 12 months when the regiment formed in 1861 (Cos. C and D, both from the Lexington, KY area). Woodward and some of his two companies (the old Oak Grove Rangers) split from this regiment in June of 1862 with some of Co. A going to serve under Forrest. The rest will be the basis of Woodward's Kentucky Cavalry Battalion which Woodward organized for 12 months service in July, 1862. According to the KY Adjutant General records, this battalion started service in the field on August 1, 1862. I cannot find how many companies made up this battalion but it was typically 3-4 for a battalion. Clarksville is taken on August 18th, 1862 by this command (and Adam Johnson's). The Confederate War Department, by this time, was only taking 3 years units and by year's end, this demand reached Woodward and the battalion disbanded in December, 1862.
On December 9, 1862, Woodward raised his third command, the 2nd Kentucky Cavalry, at Williamsport, TN. Co. A was formed from the remnants of his battalion (those men who decided to serve for three years) and the rest of the companies were newly raised as well as some companies that had raised earlier but had not yet affiliated with a regiment (like Co. E, all KY men). Co. B had some earlier formation as of September, 1862 (which included 2 Clarksville men) but did not enlist until December 9th. The regiment also contained a Louisiana (raised April, 1862) and a Virginia company (raised May, 1862) and the regiment did include a number of Tennessee men.
The unit was renumbered to the 15th Kentucky cavalry when his enrollment paperwork got to the War Department since the 2nd Kentucky Cavalry, raised by Col. John Hunt Morgan, was enlisted into CS service in June, 1862 and that number was already taken. The 3rd through 14th KY Cavalry were already serving so those numbers were also gone. Hence the renumbering to the 15th KY Cavalry. This is the proper designation for Woodward's command from this point onwards not the 2nd.
Woodward was court-martialed four times, suspended from command once and reprimanded once. The Adjutant General records note his horrible lack of paperwork filed with the War Department, which might well explain why we have never seen his report of the taking of Clarksville or Riggins Hill. On a drunken spree, he rode into Hopkinsville, KY stating that he could single handedly take the town and was shot and killed in August, 1864.
Woodward's 15th KY Cavalry served with Forrest in the West Tennessee raid of December, 1862 and fought at Parker's Crossroads as part of Forrest's Brigade.
I hope this has been helpful.
Clarksville Civil War Roundtable