As an amateur, he won a heavyweight silver medal at the 2007 World Championships and gold at the 2008 Olympics.

Chakhkiyev beat Jasur Matchanov inside the distance to become 2006 Military world champion at 201 lbs.

He also beat Cuban Osmay Acosta 24:15 at the (team) World Cup 2006 but Russia lost.

In 2006 he lost to world class (silver medallist 2005) fellow southpaw Roman Romanchuk at the Russian Championships but defeated him 28-25 in 2007 to win the Russian national title 2007.

At the world championships he defeated among others Elchin Alizade of Azerbaijan 17-6 and John M'Bumba to reach the final where he lost 6:7 against Italian Clemente Russo.