Zippy Chippy's 100th loss occurred on September 10, 2004, in the Northampton Fair at the Three County Fairgrounds. He went off at odds of 7-2, making him the second betting choice; however, Zippy Chippy finished last. In December 2004, he retired from racing to become an outrider pony at his hometown track, Finger Lakes racetrack in Farmington, New York, where he'd been banned from racing on September 8, 1998, after failing to leave the gate with the rest of the field for the third consecutive time. As an outrider pony, he escorted horses in the post parade and led them to the gate.