Smith signed with Tommy Taylor's Leyton Orient in August 1997, with a tribunal setting the fee at £42,500. He scored ten goals in 51 games in 1997–98; Orient would have finished one point outside the Third Division play-offs had they not been deducted three points. He captained Orient to the play-offs in 1998–99, and converted a penalty in the shoot-out victory over Rotherham United at the semi-final stage. However his team were beaten 1–0 by Scunthorpe United in the Wembley final. Over the course of the campaign he scored ten goals in 49 appearances.