Mary J. C. Anderson and Ellen G. Jackson
1866: Mary J. C. Anderson and Ellen Garrison Jackson Clark vs. Baltimore Railroad Company
Anderson and Jackson, two Black schoolteachers, were thrown out of a railroad waiting room by Adam Smyzer of the Baltimore Railroad Company. They sued, claiming that the Civil Rights Act of 1866 gave them the right to travel as any white person would.
Note that the Sun article mentions that both women are schoolteachers, suggesting that they are professional and orderly.
The Baltimore Sun, May 17, 1866: Local Matters
Screenshot: America's Historical Newspapers
The Sun, May 21, 1866: Local Matters
Screenshot: America's Historical Newspapers
By May 21, Smyzer chose to have his trial conducted "by a jury of his peers" who likely would not have convicted him. The case never went to trial, and was not mentioned in future news articles.
What happened? According to historian David Bogen in Precursors to Rosa Parks, the case was initially meant to come before sympathetic civil rights judge Hugh Lennox Bond. But when Smyzer requested a jury, any chance of Anderson and Jackson winning was lost.
The Black Activism Project further notes that the case was dismissed by a grand jury in July.