Cupertino Middle School After School Sports Schedule for the 2008-2009 School year. Season 1a Cross Country- Tryouts begin Sept. 2nd for both boys and girls. Season 1 Boys Volleyball & Girls Softball- Tryouts begin Sept. 2nd Season 2 Girls Volleyball & Boys Wrestling- Tryouts begin October 13th. Season 3 Girls Basketball & Boys Soccer- Tryouts begin December 8th. Season 4 Boys Basketball & Girls Soccer- Tryouts begin Febuary 4th. Season 5 Track & Field- Practice begins April 6nd. Connect to our After School Sports Web Page for further information.