The Miles Davis Quintet was an American jazz band from 1955 to early 1969 led by Miles Davis. The quintet underwent frequent personnel changes toward its metamorphosis into a different ensemble in 1969. Most references pertain to two distinct and relatively stable bands: the First Great Quintet from 1955 to 1959, and the Second Great Quintet from late 1964 to early 1969, Davis being the only constant throughout.

Milestones is a studio album by Miles Davis. It was recorded with his "first great quintet" augmented as a sextet and released in 1958 by Columbia Records.