Regarding DeWitt Clinton "Major" Lipe....

"Major" was a nickname, not a military title. He was captured just north of the Cabin Creek crossing on the Texas Road. He and a few others were sent to spy on the coming US supply train from Ft Scott. Their horse tracks were visible in the tall grass due to a heavy dew. Lt Luke Parsons led a detachment to encircle and capture them. They were brought to Ft Gibson where he convinced his captors to let him enlist in a Union regiment. These events are documented in Wiley Britton's book 'Memoirs of the rebellion on the border, 1863', in Robt Peck's memoirs in the National Tribune, "Wagon Boss & Mule Mechanic", and, if I recall correctly, the captives are named in a letter written by Watie in "Cherokee Cavaliers" (Dale & Litton)

The NPS Civil War Soldiers & Sailors system shows:

David Lipe (First_Last)
Regiment Name 14 Kansas Cavalry
Side Union
Company L
Soldier's Rank_In Pvt.
Soldier's Rank_Out Pvt.
Alternate Name DeWitt/Lipe
Notes
Film Number M542 roll 6

There is a pension card for him which shows:

Lipe, De Witt
Co. L, 14th Regt Kans Cav
Died: Dec. 6, 1916, Claremore, Oklahoma

Ken