The term 'YOU MAY DO AN OLLIE WITH IT' can be solved by the 10-letter word SKATEBOARD. A skateboard is a type of sports equipment that consists of a flat board with four wheels attached to it. It is used for recreational activities such as skateboarding, longboarding, and freestyle boarding. Skateboarding is a popular sport in which riders use their skateboards to perform tricks and stunts. An Ollie is a type of trick in which the rider jumps into the air and then lands back on the skateboard.