the quarter-final stage of the Emir of Qatar Cup and Mahmoud scored 2 goals in that competition. Al-Gharafa Mahmoud transferred to Al-Gharafa in 2006 and he would stay there for the next 5 years. Al-Gharafa finished as runners-up of the 2006–07 Qatar Stars League, and Mahmoud's 19 goals saw him take the Golden Boot award for the first time in his career. Al-Gharafa were runners-up of the Qatar Crown Prince Cup and Mahmoud scored 1 goal, in the semi-final. They were knocked out of the Emir of Qatar Cup in the semi-final, and Mahmoud scored 1 goal, in the quarter-final. Mahmoud started the season by winning the 2007 Sheikh Jassim Cup and scoring 2 goals in the final, both in extra-time. Mahmoud won his first Qatar Stars League title in 2007–08 and scored 16 league goals, the 4th-highest amount in the league. Al-Gharafa lost the final of the Qatar Crown Prince Cup, with Mahmoud scoring 2 times in the semi-final. They also lost the final of the Emir of Qatar Cup, and Mahmoud scored 3 goals in that competition including 1 in the final. Al-Gharafa were knocked out of the group stage of the 2008 AFC Champions League and Mahmoud scored 1 goal in that competition. Al-Arabi (loan) Mahmoud joined Al-Arabi at the start of the 2008–09 season on loan and won the Sheikh Jassim Cup with the club. He scored 2 league goals for Al-Arabi in the 2008–09 Qatar Stars League. Return to Al-Gharafa Mahmoud returned to Al-Gharafa midway through the season and scored 1 goal for them in the 2008–09 Qatar Stars League, as they were crowned the league champions again. He played in the Qatar Crown Prince Cup but Al-Gharafa lost the semi-final to Qatar SC. However, they won the 2009 Emir of Qatar Cup and Mahmoud scored 3 goals in that competition. Mahmoud won the league title for the third straight time with Al-Gharafa in this season, and he scored 21 goals which earned him the Golden Boot award again. He scored 4 goals in the 2009 Sheikh Jassim Cup, where Al-Gharafa were knocked out in the semi-finals, and 3 goals in the 2009 Qatari Stars Cup (including 2 in the final) which Al-Gharafa won. In the 2010 Qatar Crown Prince Cup Final, Mahmoud scored 2 goals to lead Al-Gharafa to yet another cup win. Al-Gharafa were knocked out of the 2010 Emir of Qatar Cup