The 30-year-old Chhetri was chosen for the award on the basis of votes from coaches of I-League Clubs. He led Bengaluru FC to its maiden I-League title in the first year of its participation.
Chhetri, who had also won the award in 2013 will be presented a cash prize of Rs 2 lakh besides a trophy, an AIFF release said.
This is his third 'AIFF Player of the Year Award' in four years and fourth overall. In the process, he overtook legendary I M Vijayan's feat of winning it three times.
In 2014, Chhetri finished as the highest Indian goal-scorer in I-League with 14 strikes.
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Meanwhile, Manipuri striker Bala Devi was declared the '2014 AIFF Woman Footballer of the Year'.
In 2014, Bala Devi scored 16 goals to help India retain the SAFF women's crown in Islamabad. The 24-year old Bala Devi would be presented Rs 1 lakh, besides a trophy.
AIFF also named Sandesh Jhingan as the '2014 Emerging Footballer of the Year'.
Western India Football Association bagged the 'Award for the Best Grassroots Development Programme'. In 2014, WIFA conducted 19 grassroots festivals and five GR courses besides training 128 grassroots leaders.
Kerala's Santosh Kumar was named '2014 AIFF Best Referee' while Manipur's Sapam Kennedy was declared '2014 AIFF Best Assistant Referee'.
All the awards will be presented in an Awards Night early next year.