Simon began playing with the S.K. Victoria Wanderers Academy since the age of 13. With the then U/14 team, Simon used to play as a Striker but after the next season, his then Coach Brian Azzopardi decided that Simon's natural position was that of a defender. Simon is a product of the S.K. Victoria Wanderers Academy.

Simon's favorite position is that of a right fullback but sometimes was utilized as a central defender. Simon has represented the Gozo F.C. both in the MFA First Division and MFA Second Division League. Simon was also the team captain of the Under 19 and Under 21 team and during that spell the club won two separate leagues, one in each category.

Honors won with the Club

• Under 19 League - 2005/2006
• Under 21 League - 2003/2004
• Second Division Challenge Cup - 2006/2007 and 2007/2008
• Second Division Knock Out - 2002/2003 and 2007/2008
• Second Division League - 2007/2008
• GFA Cup - 2008/2009
• Freedom Cup - 2008/2009
• Independence Cup - 2010/2011

Personal Honors

• S.K.V.W. Under/16 Best Player - 2000/2001, 2003/2004
• S.K.V.W. Under/19 Best Player - 2005/2006
• S.K.V.W. Under/21 Best Player - 2002/2003
• G.F.A Under/19 Player of the Year - 2005/2006
• S.K.V.W. Most Dedicated Player - 2008/2009