In 1999, the club entered administration with debts estimated to be around £400,000. In October 1999, the club was bought by John Duly after a period of 2 months in administration, with Billy Smith appointed as manager. At the time, the Reds were second-bottom, but the club went on to finish in 12th place, 6 points above the relegation zone. Whilst the 2000-2001 season saw Town finish 11th, Crawley were much improved in a 2001-2002 campaign which saw them finish fourth. Whilst Crawley finished 7th in 2002-03, the Reds found success in the 2003-04 season, when they ended their 20-season stay in the Premier Division of the Southern League by winning the division with 84 points, 12 points clear of second-placed Weymouth, and winning the Southern League Cup for the second successive season. The title was secured with four matches remaining with a 3–0 victory at Welling United, sparking celebrations from a large travelling contingent. Crawley would now be playing in the Football Conference, the highest level of non-League football, for the first time in their history.