Simon signed from Peterborough United along with Matthew Etherington in January 2000. The attacking winger didn’t need to wait long for his breakthrough into the first team.
During an FA Cup tie with Stockport Davies came on two grab a brace. Davies began to establish himself as a permanent fixture in the Spurs team, scoring 18 goals in 119 starts. In 2005 Davies was subject to interest from Everton and soon left the Lane.