 Beginning his career at non-league Edgware Town in 1993, McGleish was soon scouted by league club Charlton Athletic.As he was only aged 20, McGleish was sent out on loan to Leyton Orient for the first of his four spells at the club.It was here that he began to make a name for himself, despite it only being a short-term loan he made six appearances and score his first senior goal in league football.