He served as a councillor for St Mark's ward in Surbiton in Kingston upon Thames, and in the 1997 general election he stood in the safe Labour seat of Bootle. Matthews was selected as a Conservative candidate for the 2009 European Parliament election and was placed third on the Conservative party list for the East Midlands. He was not elected. On 12 October 2011, MEP for the East Midlands regionRoger Helmer, announced that he would resign from the European Parliament at the end of the year. Helmer expected to be replaced by Matthews who had been next on the Conservative party list in the East Midlands. However, after there was uncertainty whether the Conservative Party would approve Matthews as the new MEP, Helmer announced he would delay standing down until the position was clarified and Matthews confirmed as his successor. The Conservative party was reported to be looking into golliwog dolls featuring on the front cover of a book on political correctness published by Bretwalda Books. It was later reported that Matthews was not personally involved in publishing the book. In March 2012, Helmer defected to UKIP and remained an MEP; he was re-elected in 2014. For the 2014 European Parliament election Matthews was again placed third on the Conservative party list for the East Midlands and, again, missed being elected. In 2014, Matthews took up a position as National Campaigns Director at Better Off Out. He led Better Off Out's campaign for Britain to Leave the European Union, liaising with the official campaign as well as with Leave.EU and Grassroots Out. During this time, he supervised the production of leaflets, posters and other campaign materials as well as organising their distribution to the public in the run up to the 2016 European Union membership referendum. Matthews finally became a MEP for the East Midlands on 29 June 2017, replacing Andrew Lewer after Lewer was elected to the House of Commons. He was not elected in the 2019 European Parliament election. Matthews reportedly thinks the Treaty of Lisbon could enable the European Commission to invade Britain should the country ever attempt to leave the European Union, or to request a German panzer division be sent to London if the situation should warrant it. Matthews is the Conservative candidate for Leicestershire Police and Crime Commissioner in 2020.