Danny,
On the south side of Clear Boggy (aka South Boggy and Boggy River), south of Frisco ("Old Stonewall") is a Cochran's Cemetery -- Is this where Robert is presumed to be buried? Just east of south from Frisco on the south side of Clear Boggy is supposed to be the location of the Collin's Institute, moved there from Perryville in the late 1850s. On some old maps is shown Cochran's Academy but it is shown on Middle Boggy in the Choctaw Nation instead of Clear Boggy in the Chickasaw Nation. Unless there was another school by that name, I assume the maps to be incorrect as to the location and creek upon which the school was located. The Ft Smith-Ft Arbuckle road passes through Perryville where it intersects with the 'Texas Road'.

The portion of the map from the Chronicles Vol 39, No 1 "Lieutenant Averell's Ride, 1861" is shown below. The full article is at http://digital.library.okstate.edu/Chronicles/v039/v039p002.pdf

The Dragoon's route crossed the Canadian at the mouth of Little River (Old Fort Holmes, Edward's Trading Post). Traveling south by this route from the Frisco area it passes the Wapanuka Academy (Rock Academy) on Delaware Creek and Colbert's Mill on Pennington Creek, north of Tishomingo. Traveling further west toward Ft Arbuckle would lead to the vicinity of one of communities named "Oil Springs" where Chickasaw Governor Winchester Colbert lived. Confederate Reports say that Phillips Expedition came down the road passed Colbert's Mill and the Rock Academy. Phillips wrote to Gov. Colbert that he came by his house to see him.

After the 'Battle of Middle Boggy', Phillips says Jumper retreated to Ft Arbuckle. On his return trip, Phillips writes from "Old Fort Arbuckle - Little Rivertown". This is perplexing. "Old Fort Arbuckle" was on the south side of the Canadian south of present Konawa and well south of Little River. The mouth of Little River was the site of "Old Fort Holmes". I wonder whether Phillips crossed the Canadian at Old Fort Arbuckle or if he was really at Old Fort Holmes. It seems a town named "Little Rivertown" would be on the Little River -- Old Fort Arbuckle is not on Little River but Old Fort Holmes is.

Phillips says the 'battle' with Jumper was on Middle Boggy and that Camp Kagi was 20 miles south on South Boggy. If this is precise, I believe Cochran's on Clear Boggy to be the location of Camp Kagi (or Kahi) in the Chickasaw Nation. The battlefield (Camp Kansas) would be 20 miles northeast in the Choctaw Nation. However, I wonder if Phillips thought Clear Boggy was Middle Boggy and that Cochran's was on Middle Boggy in the Choctaw Nation -- as erroneously shown on pre-1900 maps. The battle may have been at/near Cochran's -- a good place for Jumper et al to camp -- and Camp Kagi 20 miles south, perhaps on Blue River.

There were likely other Federal Scouts in this area, especially after February 1864 when Phillips sent foraging details into the western Creek Nation and into the Seminole Nation to get corn. Adair mentions Federal Scouts were spotted around Camp McIntosh (between Ft Arbuckle and Ft Cobb). However, it seems possible that Cochran was killed during Phillips Feb 1864 Expedition and perhaps in connection with the Middle Boggy engagement. Do you know the date of death of Robert Cochran?

The paragraph re Boggy Depot is a little confusing but I should note that Harris was Chickasaw Governor at the beginning of the war, succeeded by Winchester Colbert. From the Chronicles of OK, Vol 11, No. 2: "The line of the Texas Road from the crossing of the Canadian, south of present Eufaula, was established after the founding of Fort Washita. Before that, the Texas Road out of Fort Gibson followed the old Leavenworth Trail, crossing the Canadian at the mouth of Little River, in Hughes County. Thus, for travelers both from the north and the east toward Fort Washita, the crossing on Little (or North) Boggy, about two miles southwest of present Stringtown was an important point. A. W. Geary, an intermarried Choctaw, established his residence, an extensive farm, and other improvements here at an early date." … [the Overland Route passed through] "Geary's Crossing on Little (North) Boggy, Davis Crossing on Middle (Muddy) Boggy, Boggy Depot Crossing on Clear Boggy, Nail's Crossing on Blue, thence southwest by the prairie country past the head of Island Bayou and on to Colbert's Ferry."
The references to 'Little Boggy' related to the merged Texas Road and Ft Smith-Boggy Depot Road (Butterfield Route), far distant from the California Road (along the Canadian) and the Ft Smith-Ft Arbuckle Road in Hughes, Coal, Pontotoc Counties. Little Boggy is not mentioned in any reports regarding the Middle Boggy Battle. Jerry Coffee's posts give a good description of this area from the junction of the Ft Smith-Boggy Depot Road with the Texas Road, near present Stringtown, and Geary's and McKinney's in that area.
I cannot find any sources that lead me to believe that the Battle of Middle Boggy was anywhere in the vicinity of present Atoka or Stringtown. All primary sources seem to point to this Leavenworth Road to Coal or Pontotoc Counties in the Frisco vicinity.