Issue No. 1 - Released in late 2010, the debut issue of Headmaster features 88 full-color pages of original projects produced by Benjamin Fredrickson, Conner Habib, Jamil Hellu, Sholem Krishtalka, Steven Miller, Ben Piciorel, William Rudolph, Jason Tranchida, Jorge Ureña, and Tannar Veatch. Cover by Jason Tranchida.
Issue No. 2 - Released in the summer of 2011, Headmaster no. 2 features 88 full-color pages of original man-loving projects by Stéphane Barbier, Jesse Burke, Heyd Fontenot, Krys Fox, Steven Frost, M Kitchell, Steve Locke, Johnny Murdoc, Joseph Segal, and Thomas Weidenhaupt. Cover by Jesse Burke.
Issue No. 3 - Headmaster no. 3 features ten projects in the fields of anatomy, anthropology, astronomy, etiquette, film studies, and history by Peter Cochrane, Alan Cumming, Chris Ironside, Ivan Lozano, Matthew Lawrence, Gabriel Martinez, Walker Mettling, Matias Uris, Jim Verburg, and Michael Wynne. Cover by Matias Uris.
Issue No. 4 - Headmaster no. 4 features original projects by artists from across the US, Europe, and the Middle East, including Liz Collins, Cassandra Complex, Zena el Khalil, House of Cach, Naima Lowe, Margo Ovcharenko, Alex Sears, Monica Shinn, and Francesca Yorke. Cover by Cassandra Complex.
Issue No. 5 - Headmaster no. 5 features original projects by Ross Bleckner, Drasko Bogdanovic, Chris Bogia, Ben Kline, littlewhitehead, Slava Mogutin, Aaron Peterman, Nathan Prouty, and Dean Sameshima. Cover by Drasko Bogdanovic.
Issue No. 6 - Headmaster no. 6 features nine projects by Alexander Chee, Ian Cozzens, Anthony DiCapua, Luka Fisher, Ted Gideonse, Matthias Herrmann, Matt Lambert, Barry Marré, and Stephen Scott Smith. Cover by Matthias Herrmann.
Issue No. 7 - Headmaster No. 7 was released in April 2015. The issue features original projects by flanKo, Josh Nece, Dave Ortega, Andrew Printer, Jaanus Samma, Pacifico Silano, Matt Underwood, J.R. Uretsky, and Jade Yumang.
Issue No. 8 - Headmaster No. 8, The Village People Issue, features original projects by Mark Blane, Emmy Bright, Skylar Fein, Nicholas Galanin, Alan Ruiz, Micah Salkind, Joe Sinness, Wolfgang Tillmans, Bernhard Willhelm, and Derrick Woods-Morrow.