A press-fitting device includes: a workpiece holding portion; a one-side pressing unit configured to press either one of a press-fitting tool and a backup tool against a workpiece in a first direction while performing three dimensional position adjustment thereon; an other-side pressing unit configured to press the other one of the press-fitting tool and the backup tool which is not pressed by the one-side pressing unit, against the workpiece in a second direction opposite to the first direction, while performing three dimensional position adjustment thereon; and a press-fitting controlling portion configured to control stroke amounts of the tools in a press-fitting direction at the time of a press-fitting operation. The press-fitting controlling portion includes a stroke manipulating portion; a displacement data storing portion; and a stroke correction portion.