The league engaged in another reorganising and renaming exercise for 1999–2000 and Ashford now competed as a Southern League, Division One Eastern team. Wakeling had the team topping the league table in the autumn of 1999 as the side lost just once in 18 league matches. This unbeaten run included an Ashford Town record of eight straight league wins from 16 October 1999 to 13 November 1999, scoring 21 goals, whilst conceding only four. This winning streak equalled a previous run of wins under Neil Cugley, however the Cugley run was over two seasons, after the side won the opening game of season 1995–96, having won the last seven at the end of season 1994–95. Things then took a nosedive for Messrs Wakeling & Parker, amidst all the turmoil of the takeover and after a run of just one win in seven and the pair were duly sacked on 10 January 2000. They were replaced by Tony Reynolds and he was replaced a year later by Tommy Sampson (who had taken Deal Town to victory in the FA vase final the previous season). The team achieved a run of mid-table league finishes at this time.