— born in VA or OH:
.  William A. CUPP, b. 7 May 1808  {42, VA} 
Valentine was in Ohio by 1807, so either William is mistaken about being born in VA or he was not born in 1808.

— born in Fairfield Co., OH:
.  Mary Ann CUPP, b. 10 Sep 1809 
.  Samuel CUPP, b. 24 Feb 1814 or 1811/2  {38, OH} 

.  Elizabeth CUPP

1.  Lyman Chalkley.  1912.  Chronicles of the Scots-Irish Settlement in Virginia: Extracted from the Original Court Records of Augusta County, 1745-1800.  3 vols.  Commonwealth Printing Co., Rosslyn, VA (reprinted 1965, Genealogical Publ. Co., Baltimore, MD; online in the USGenWeb Archives):

Vol. 2	RECORD OF MARRIAGES IN AUGUSTA COUNTY... NOTE.--First line, date of bond, principal and surety; second line, principal and bride...
p. 304	1793--December 21, Valentine Cup and George Falls (German), surety. Valentine Cup and Mary Falls, daughter of Geo. Falls.

2.  Census Index:  U.S. Selected Counties, 1790 (Broderbund CD-311):  not found, as expected.

3.  "Taxpayers in Bloom Township, Fairfield County, Ohio, 1806."  Extracted from History of Fairfield County, Ohio, by Hervey Scott, 1877, p. 40 (online at the Foor/Foore/Fuhr Genealogy web site).  There are no CUPPs (or variations) on this list, so we can pinpoint Valentine's arrival in the county to 1806/7.

4.  Census Index:  U.S. Selected Counties, 1800 (Broderbund CD-312):  there was no Ohio census in 1800; tax lists for some counties are substituted on the CD.

1807 Tax List

Cop, Valentine

OH

Fairfield Co.

p. 5

He is the only COP/CUPP/&c. in Ohio on this CD.

5a.  Census Index:  U.S. Selected Counties, 1810 (Broderbund CD-313):  the 1810 Ohio census was lost (except for Washington Co.); tax lists for some counties are substituted on the CD.

1810 Tax List

Cup, Valentine

OH

Fairfield Co.

p. 10

Valentine is the only CUP/CUPP in Fairfield Co. on this CD.

5b.  Thelma Blair Lang.  1986.  "Index to Tax List of Ohio for 1810, Fairfield County."  Pages 136-138 in Ohio Source Records: (excerpted and reprinted) from The Ohio Genealogical Quarterly.  Genealogical Publ. Co., Baltimore, MD (Broderbund CD-177):

p. 136

...Cup, Valentine...

Valentine is the only CUP/CUPP in Fairfield Co.

6.  1820 Census Index and Digital Images (online at Ancestry.com; Image #3 of 4 — indexed "Cap"; extracted by Diana Gale Matthiesen):¤•

1820

OH

Fairfield Co.

Walnut Twp.

p. 104

Ln. 15

Valentine Cup

131201-10010-0-300

These data indicate:

No. & Sex	Age Class	Therefore Born	Individuals Inferred
1 male	9 or under	1810-1820	= Samuel (b. 1814)
3 males	10-15	1804-1810	= William (b. 1808) = Male B = Male A
1 male	16-18	1801-1804	= Daniel (b. 1801)
1 male	19-25*	1794-1801	= John (b. 1798)
1 male	45 or over	in or bef. 1775	= Valentine (b. 1765/6)
1 female	9 or under	1810-1820	= Mary (b. 1809)
1 female	26-44	1775-1794	= Mary (b. 1772)
3	persons engaged in agriculture
*In the 1820 Census, the third column is age class 16-18 and the fourth column is age class 16-25; therefore, any individual in column three is duplicated in column four.  By subtracting the number in column three from the number in column four, you can create an age class "19-25."

Listed three lines from son-in-law, William LAMB. 

7.  1830 Census Index and Digital Images (online at Ancestry.com; Image #31 of 34; extracted by Diana Gale Matthiesen):¤•

1830

OH

Fairfield Co.

Walnut Twp.

p. 199

Ln. 26

Valentine Cup

002 210 001 - 010 210 100

These data indicate:

No. & Sex	Age Class	Therefore Born	Individuals Inferred
2 males	10-14	1815-1820	=
2 males	15-19	1810-1815	= Samuel (b. 1814)
1 male	20-29	1800-1810	= William (b. 1808)
1 male	60-69	1760-1770	= Valentine (b. 1875/6)
1 female	5-9	1820-1825	=
2 females	15-19	1810-1815	=
1 female	20-29	1800-1810	=
1 female	40-49	1780-1790	= Barbara

Listed two lines from son-in-law, William LAMB. 

8.  1840 Census Index and Digital Images (online at Ancestry.com; Image #21 of 24; extracted by Diana Gale Matthiesen):¤•

1840

OH

Fairfield Co.

Walnut Twp.

p. 352B

Ln. 30

Cupp Valentine

001 010 000 100 - 000 100 010

These data indicate:

No. & Sex	Age Class	Therefore Born	Individuals Inferred
1 male	10-14	1825-1830	=
1 male	20-29	1810-1820	=
1 male	70-79	1760-1770	= Valentine (b. 1765/6)
1 female	15-19	1820-1825	=
1 female	50-59	1780-1790	= Barbara

List is roughly alphabetized, so no neighborhood reconstruction is possible.

9.  1850 Census Index/Images (online at Ancestry.com; Image #48 of 51 — indexed as "Valentine Capp"):  Walnut Twp., Dist. 41, Fairfield Co., OH, p. 219B, 1329/1329, enumerated 6 Sep 1850 (extracted by Diana Gale Matthiesen):¤•

Cupp Valentine	84	M	None	16160	Penn
"  Barbary	40	F			Va

Living between son William CUPP and son Samuel CUPP, who is listed two households from daughter, Catharine (CUPP) LAMB. 

10.  1860 Census Images (online at Ancestry.com; Image #5 of 54):  Pleasantville P.O., Walnut Twp., Fairfield Co., OH, p. 227A, PN 187, 1366/1365, enumerated 3 Aug 1860, official enumeration date 1 Jun 1860 (extracted by Diana Gale Matthiesen):¤•

Barbara CUPP

72

F

200

Va

Living next to son William CUPP on one side; and, in the other direction, three households from son, Samuel CUPP, who is three households from her daughter, Catharine (CUPP) LAMB. 

11.  Fairfield County, OH, CUPP Grantee Land Records  (online at Lynn Cupp's web site):

Grantee	Grantor	Instrument	Date	Book	Page
Volentine CUP	William/Susannah GARY	Deed	1830	S	90
Valentine CUPP	David/Ann BEAM	Deed	1833	U	429
Valentine CUP	Daniel BARKER et al	Deed	1833	V	173
Valentine CUP	John M./Ann SNIDER	Deed	1834	X	35
Valentine CUP	Henry/Frances E. STANBERY	Deed	1839	5	105
William/Valentine CUPP et al	Solomon/Cristianna SPANGER	Misc	1844	10	65

Valentine was the second CUPP to buy land in the county.  The first was Conrad CUPP in 1825.

12.  Ruth Bowers & Anita Short.  1989.  "Fairfield County, Ohio — Will Abstracts 1812-1815."  Pages 437-442 in Vol. I of Gateway to the West.  Genealogical Publ. Co., Baltimore, MD (Broderbund CD-175):

BLACK, John - dated 8-29-1814; recorded 1-23-1815. Wife, Sarah. Son, James Black. Three daughters: Mary, Sally and Lydy.  Executors: Robert Black and Jesse Pew. Signed: John (his mark) Black. Witnesses: John Hampson and Valentine Cup. (37)

13.  Anon.  1886.  History of Seneca County, Ohio.  Warner, Beers & Co., Chicago (online at Heritage Pursuit):

p. 857

Hopewell Township WILLIAM CUPP, retired farmer, Tiffin, was born May 7, 1808, in Augusta County, Va., son of Valentine and Mary (Fall) Cupp, of German descent. Valentine Cupp was twice married and had nine children, of whom six survive, two — David and William — being residents of Ohio.  Our subject was brought to Fairfield County, Ohio, by his parents in 1808, his father carrying him in front of him on his horse most of the way.  They settled in Walnut Township, Fairfield Co., Ohio, where the father purchased a farm on which he passed the remainder of his life...

Valentine is on the 1807 tax list of Fairfield Co., OH.  For complete sketch, see William CUPP's page. 

14.  Messages in the Cupp Family Genealogy Forum (online at GenForum.com).

15.  WorldConnect / Ancestry World Trees (online at RootsWeb.com/Ancestry.com).

16.  Broderbund.  World Family Trees.  Vol. 25, Pedigree #1709.