
After beginning his early career in the Tottenham, Maher moved to Southend United on a free transfer on 23 January 1998. He quickly broke into the first team, making 18 appearances for the first-team. During the 1998–99 season, Maher scored his first career goal in a 1–1 draw with Rochdale.
Over the next 10 years Maher was a virtual ever-present for Southend, rising to be team captain and subsequently club captain. During this time he made more than 400 total appearances for the club, and captained Southend to promotion from Division Two to the Championship in successive seasons. When, during the 2007–08 season it became clear that Maher was no longer an automatic first choice he chose to look for opportunities elsewhere.
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