The Highlanders began a slow fall from the top of the hill starting around 2001, and had losing seasons from 2002–08. After an 0–10 campaign in 2008, the 2009 team rebounded to 6–5 and made the Northern Region playoffs, losing in the first round to Robert E. Lee High School. Their six wins broke the VHSL record for the best turnaround by a team. The 2009 season highlight came in beating rival school Langley High School in a 35–34 overtime bout, winning the Rotary Cup, the trophy given to the winner of every sporting match between the two schools, and the Battle of the Scots for the 1st time in 12 years. The Highlanders started the 2010 season 8–0 overall and 5–0 in district play, the best start to the program in 15 years. The Highlanders began their 2010 campaign preseason-ranked last in the district by the Washington Post, with a 1-star rating according to the online preview. After the 8-0 start in 2010, the Highlanders closed the season with an 8-3 record after losses to Stone Bridge and Langley, followed by a loss in the first round of the regional playoffs to Hayfield Secondary School.