The first part of season 7 begins in January 1969, several weeks after the Thanksgiving 1968 ending of season 6, and ends in July 1969, with characters dealing with the dynamics of lives and offices being split between New York and Los Angeles.

Season 6 takes place between December 1967 and November 1968.

Season four takes place between November 1964 and October 1965. It is set at the new and considerably more modern advertising agency, Sterling Cooper Draper Pryce. The main narrative of the fourth season is driven by Don Draper's identity crisis. As Don falls deeper into existential despair, he begins regularly meeting with women of loose moral character and faces debilitating alcoholism.

Season three takes place six months after the conclusion of the second season and ends in December 1963. It chronicles the end of the "Camelot era" as the characters go through immense change in their professional and personal lives.

Season two takes place between February and October 1962, culminating with the Cuban Missile Crisis. It expands on Peggy's rise in the workplace and the marital strife between Don and Betty Draper as Don's infidelities further intrude on his family life. The second season also introduces an unknown acquaintance of Don Draper. Draper is corresponding by letter with this unseen acquaintance in secret.