Sometimes labelled the “Cinderella” arm of Athletics, Cross-country is by no means a Cinderella sport at Woodlands College. Under the strong guidance of top runner and coach Mr Darrel Laybourn, Woodlands participates in two cross country leagues: namely the Boksburg D6 League and the SISA League. All Boksburg D6 meetings take place at the Boksburg Stadium. Woodlands annually enters a large team under the guidance of Mr Laybourn who has had managed to encourage and motivate many children to train early in the mornings, and then run competitively. Woodlands Cross country runners regularly progress to the Boksburg Area Championships, as well as qualify for the Regional Championships.

Woodlands also participated in the SISA League (only private schools participate in this league). The Woodlands athletes once again performed very well and are exposed to various venues, including one event hosted by Woodlands.