A stump pulling apparatus comprises a frame, a pair of arms, a pair of stump-engaging wheels, and a drawbar. The pair of arms are pivotally mounted to the frame. The pair of stump-engaging wheels are each rotatably mounted on the pair of arms at a rear end of the corresponding one of the pair of arms. The drawbar includes a front segment, configured to engage the vehicle for towing the stump pulling apparatus and slidably coupled to the rear segment, a rear segment coupled to each of the pair of arms, and a displacement cylinder coupled to and intermediately disposed between the front segment and the rear segment. When the front segment of the drawbar is pulled forward, the displacement cylinder provides a forwardly-acting force on the rear segment, which pivots the pair of arms toward each other, thereby forcibly bringing the stump-engaging wheels together.