In November 1997, Bennett left the Labour party and joined the United Kingdom Independence Party (UKIP). In April 1999, he became the Campaign Manager for UKIP's Eastern Region campaign and, in July 1999, he became Political Assistant to Jeffrey Titford, UKIP MEP, a post he held until February 2001. In January 2000, he co-founded the UKIP's "Metric Martyrs Fund" with Jeffrey Titford, and published leaflets encouraging traders to defy the new laws making it an offence to sell fruit, vegetables and other "loose goods" using weighing scales calibrated in pounds and ounces. He stood for the UKIP in Harlow in the 2001 General Election, where he finished fifth with 1,223 votes (3%).