I think I have found who Benjamin was
In Rappahannock county, VA there is a chancery file of Cubbage vs. Cubbage concerning the estate of Archibald Cubbage who died in 1854
Mentions two Sons, Benjamin and Roland.
One son John moved to Georgia and was dead at the time. One daughter Nelly, was dead leaving 2 sons Augustine and Albert. I know Augustine Cubbage of Page/Madison counties was a son of John Smith and a Penelope Cubbage. So I think this Nelly, was a Penelope. Also the chancery file seemed to imply that Benjamin had gone to Shenandoah County.
So this info places Benjamin Cubbage in family like so
1.John Cubbage d. 1796 Culpeper Co m. Mary Jenkins
..2. George Cubbage
..2. Thomas Cubbage m. Susan
...3. William Cubbage, Sr.
...3. Jacob Cubbage
..2. Archibald "Acre" Cubbage m. Elizabeth Nicholson (daughter of John & Anne)
...3. Benjamin Cubbage
...3. Roland Cubbage
...3. John Cubbage
...3. Penelope Cubbage
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