Northwood gradually climbed through the divisions of the Isthmian League under Tony Choules winning the Isthmian Charity Shield in 2002, and then reaching the Premier Division in 2003 after winning the 2002/03 Isthmian Division One North. The side was then switched to the Southern League in 2005, where they remained until 2007. However, after relegation from the Southern League Premier Division they were moved "sideways" to the Isthmian League Division One North. Despite relegation, Northwood did lift the 2006/07 Middlesex Senior Cup as they beat Conference South outfit Hayes 4–2 on penalties, although it was the only real bright point in a disappointing season. Since then Northwood have seen several managers come and go. Dave Anderson was the most successful in that period as he helped the club finish 6th and 10th, in the 2008–09 and 2009–10 respectively, before departing in March 2010.