He joined Chelsea as a youth player and made his debut for the Blues against Swindon Town in September 1963 aged only 17. A talented and hard-running midfielder, usually wearing the number 4 shirt, he was known for his dedicated attitude to the game and went on to become a regular and eventually club captain. Hollins played 592 games, and scored 69 goals in his first spell at Chelsea, and was part of the successful Chelsea sides of the mid-1960s and early 1970s. After establishing himself in the Chelsea side in 1964, he rarely missed a game over the next decade, appearing in 400 out of a possible 420 league games, at one point making 167 consecutive appearances, a club record.