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- O'Brien Smith to James Madison, June 10, 1802. (1)
- O. Johnston to Unknown, May 17, 1812. Forwarded to James Madison. (1)
- O. Towles , November 26, 1787. Certification of Service of J. Turnley. (1)
- Obadiah B. Brown to James Madison, August 22, 1815. (1)
- Observations of a Botanical Garden. (1)
- October 27, 1808. The Spirit of Seventy-Six newspaper article regarding correspondences between Thomas Jefferson and James Monroe on the eve of the 1808 election. (1)
- October, 1782. Note in French to United States Congress. (1)
- Office of Discount and Deposit, May 5, 1806. Nineteen blank checks dated May 5,1805 to Aug 5,1806. All signed by James Madison. (1)
- Oliveira & Sons to James Madison, November 3, 1810. Includes account and bill of lading. (1)
- Oliveira & Sons to James Madison, October 25, 1810. With Account. (1)
- Oliveira & Sons to James Madison, October 26, 1810. (1)
- Oliver Evans to James Madison, March 8, 1814. (1)
- Oliver Pollock to James Madison, October 22, 1801. (1)
- Oliver Towles to James Madison, November 8, 1791. (1)
- Oliver Whipple to James Madison, October 22, 1811. (1)
- Oliver Whipple to Thomas Jefferson, February 6, 1809. (1)
- Oliver Wolcott Jr. to Joseph Howell, August 13, 1792. Extract of a letter from the Comptroller of the Treasury. (1)
- Oliver Wolcott Jr. to Joseph Howell, July 13, 1792. (1)
- Oliver Wolcott to James Madison, August 1, 1814. (1)
- Orchard Cook to James Madison, August 11, 1812. (1)
- Orchard Cook to James Madison, December 16, 1815. (1)
- Orchard Cook to James Madison, March 3, 1814. (1)
- Orchard Cook to Thomas Jefferson, January 20, 1809. (1)
- Ottawa Indian Chiefs-Friendship. Speech. 1812. (1)
- Overton Carr to James Madison, July 22, 1813. Receipt for installment for stock in the Potomac Steam boat Co. (1)
