| December 17, 1760 | Deborah Sampson is born | Born the oldest of seven children, Deborah was born in Plympton, Massachusetts. Her parents were poor, even though her mother descended from William Bradford, once a governor of Plymouth Colony. |
| 1770 | Indentured servant | Because Deborah's family was poor she became an indentured servant in order to pay her family's debts. She lived on a farm with the Thomas family until she was eighteen years old. |
| 1775 | Her father enlists | Deborah's father, Jonathan, enlisted in the Revolutionary War in July 1775. He eventually died a pauper. |
| 1780 | Deborah gets an idea | As a woman who enjoyed hunting, tracking, and fishing, Deborah wanted to help further the cause of American freedom. It was during this time she first had the idea to enlist in the war disguised as a man. |
| 1782 | Deborah enlists | Because women weren't allowed to enlist to fight, Deborah disguised herself as a man. She enlisted in Massachusetts using her brother's name. |
| July 3, 1782 | Her first battle | Deborah, fighting under the name Robert Shertlieff, fought her first battle in New York. She was injured by musket balls, but she was afraid the doctors would learn her secret identity so she refused medical treatment. |
| 1783 | Deborah is promoted | Deborah found herself earning a promotion. She served under General John Paterson as one of his personal waiters, and she was spared from battle for several months. |
| June 1783 | An end to the war | The Treaty of Paris was signed and ended the war, but rebellions continued to break out for a few months. During a small fight, Deborah came down with fever and the doctors who treated her discovered her secret; they did not tell anyone she was a woman. |
| October 1783 | Honorable discharge | Even though General Henry Knox eventually learned Deborah's secret, he did not reveal her true identity. She was allowed an honorable discharge from the Army at West Point. |
| April 1785 | Marriage and children | After leaving the army, Deborah Simpson resumed life as a lady. She married a man named Benjamin Gannett, and they had three children. |
| 1792 | Compensation for her labor | Once the army had discovered she was a woman, they refused to pay Deborah for her faithful service. She petitioned the courts on her own behalf, and she was eventually granted fair pay in the amount of 34 pounds. |
| 1797 | Deborah the author | Many people were impressed and intrigued by Deborah's heroics. She eventually co-authored a book about her adventures, though not all her stories were accurate. |
| 1802 | Deborah continues working | Deborah's financial needs grew, and she found herself giving lectures about her army adventures in order to earn money. Even with her lively stories, though, she did not earn enough to live off of. |
| 1804 | Paul Revere speaks on her behalf | Admiring her bravery and believing she deserved as much as any man, Paul Revere went to the Massachusetts Representative William Eustis. He asked that Deborah be given fair compensation for her time in the army, and she was at last paid a monthly pension for her service. |
| 1827 | Deborah's death | After many years of struggle and hard work, Deborah passed away on April 29, 1827. She was sixty-six years old. |
