This volume contains seventeen papers that were presented at the 2015 Annual Meeting of the Canadian Society for History and Philosophy of Mathematics/La Societe Canadienne d'Histoire et de Philosophie des Mathematiques, held in Washington, D.C. In addition to showcasing rigorously reviewed modern scholarship on an interesting variety of general topics in the history and philosophy of mathematics, this meeting also honored the memories of Jacqueline (Jackie) Stedall and Ivor Grattan-Guinness; celebrated the Centennial of the Mathematical Association of America; and considered the importance of mathematical communities in a special session. These themes and many others are explored in these collected papers, which cover subjects such as New evidence that the Latin translation of Euclid's Elements was based on the Arabic version attributed to al-Hajjaj Work done on the arc rampant in the seventeenth century The history of numerical methods for finding roots of nonlinear equations An original play featuring a dialogue between George Boole and Augustus De Morgan that explores the relationship between them Key issues in the digital preservation of mathematical material for future generations A look at the first twenty-five years of The American Mathematical Monthly in the context of the evolving American mathematical community The growth of Math Circles and the unique ways they are being implemented in the United States Written by leading scholars in the field, these papers will be accessible to not only mathematicians and students of the history and philosophy of mathematics, but also anyone with a general interest in mathematics.