Arguably a first ‘digital-analogue’ print: a portrait of Amelia Elizabeth, Landgravine of Hesse–Cassel, 1642
by Ludwig von Siegen, done with a dotting tool:
Ludwig von Siegen: Portrait of Amelia Elizabeth, Landgravine of Hesse-Cassel” (18.47) In Heilbrunn Timeline of Art History . New York: The Metropolitan Museum of Art, 2000–. http://www.metmuseum.org/toah/works-of-art/18.47 (October 2006)
With thanks to Edgar Whitley for suggesting this.