Serendipity is slippery, marked by an ambiguity it is more enjoyable to explore than to lament. This talk will visit the concept through the lens of two related disciplines — classics and archaeology, particularly classical archaeology. From one direction, we will investigate the degree to which serendipity — the name an invention of the eighteenth century AD — possesses a stratigraphy, an ancient history, and examine some of the contexts in which Greeks and Romans (and those that study them) recognized the power of unexpected conjunctions and discoveries. From the other angle, the role of serendipity in the early history, and later development, of classical archaeology will be assessed. For a field in which the act of ‘discovery’ is so important, and luck so often ascribed to the successful, serendipity is a surprisingly unpopular factor to invoke — a reluctance that is actually quite revealing. Together these two disciplinary squints at the concept will demonstrate aspects of its history, elasticity, catalytic force, and occasional humor.