York player Neil Thompson took over as caretaker manager, but he was unable to avoid relegation to the Third Division, after a defeat on the last day of 1998–99. He was appointed permanently in May 1999, but was dismissed in February 2000 with York 21st in the table. Former Hull City manager Terry Dolan was appointed and he led York clear of relegation in 1999–2000. Despite off-pitch problems at the club, York were in an automatic promotion place by late-March 2003, before finishing 10th in 2002–03. York player Chris Brass was appointed player-manager in June 2003; aged 27, this made him the youngest managerial appointment in the Football League since 1946. Having been 10th in the table in January 2004, York went 20 matches without a win and were relegated to the Conference National after 2003–04, which brought to an end 75 years of Football League membership. Brass was dismissed in November 2004 with York fourth from bottom of the table, and his assistant Viv Busby took caretaker charge before the appointment of former Derby County coach Billy McEwan in February 2005.