William O. Winston, Jr. was admitted to West Point, July 1, 1859 in the Class of 1863, which totaled 48 men. He was 19 years, 8 months, from Alabama
At the end of his first year, 43 remained in the class, he stood 41st. Five were turned back. He ranked 40th in Mathematics and 43rd in English Studies. He garnered 99 demerits for the year, 38 for the 6 months ending June 6, 1860.
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Synopsis of the Course of Studies and Military Exercises at the U. S. .ltlilitary Academy, First year
Mathematics. Prof. Church, Lieutenants Howard, Hascall, Webb.
Bourdon’s Algebra.
Legendre ‘s Geometry and Trigonometry.
Descriptive Geometry.
English Studies and Literature, Prof. French, Lieutenants Benit, Symonds, Bigggs.
Morse’s Geography.
Bullions Grammar
Vocabularies by Prof. French.
Roget’s Thesaurus of English Words.
Parker’s Aids to English Composition.
French’s Practical Ethics.
French’s Prefixes and Suffixes.
Weber’s Outline of Universal History.
Sargent’s Elocution. Composition and Declamation.
Tactics of Artillery and Infantry, Bt. Lt. Col.W. J. Hardee, Lieutenants Saxon, Dodge, Williams, McCook
Theoretical Instruction in the Schools of the Soldier and Company
Practical Instruction in the Schools of the Soldier, Company, and Battalion
Practical Instruction in Artillery
Use of Small Arms, Lieutenant Kelton, Mr. Lorentz.
Instruction in Fencing, and Bayonet Exercise.
http://digital-library.usma.edu/libmedia/archives/oroc/v1860.pdf
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In a letter to the President dated 19 June 1861, Valley Head, Alabama, he notes, "I was Cadet in the Military Academy at West Point from June 1859 till about the 1st of January 1861, at which time learning that Alabama had a majority in convention for immediate secession, I resigned my position . . . . I am in the 22nd year of my age. Have made the Military art my study during the last four years. I understand Infantry tactics and have some knowledge of fortifications and field artillery. I now tender you my services and am ready to occupy whatever position in the Regular army you may direct to be assigned me hoping and believing that I can render some aid in the defense of the Independence of our beloved South."
M331: Compiled Service Records of Confederate General and Staff Officer and Nonregimental Enlisted Men