Nicknamed "Man of Steel"[2] (Dhivehi: ދަގަނޑޭ, romanized: Dhagandey), he is regarded as one of the best players in the South Asian region.

Ashfaq moved to Brunei's DPMM FC in October 2007, and he joined VB Sports Club after two months and stayed with them until 2011.

[12] Ashfaq was born in Malé, the capital of Maldives, where he grew up with his mother and older brother Ahmed Ashfan.

[13] On 26 October 2001, Ashfaq played his very first match in 2001 POMIS Cup tournament against Thailand's BEC Tero Sasana FC, wearing the Club Valencia jersey for the very first time.

Ashfaq played his first international club tournament against Mohun Bagan of India in 2002–03 AFC Champions League qualification on 9 October 2002.

[6] On 6 April 2004, Ashfaq played his very first match in an AFC Cup tournament against Hong Kong's Happy Valley AA, scored both goals in a 2–1 win.

In October 2007, Ashfaq moved to Brunei DPMM FC on a two-month contract, which competed in the Malaysia Super League.

In FA Cup final, Ashfaq netted four times to help VB win the championship after beating Maziya by 6–4 on 31 October.

The rumors were not believed until 25 February 2011, when VB announced that Ashfaq had been stripped of the captaincy only a few days after the club had won the Milo Charity Shield.

[18] Ashfaq then went missing shortly before the team went to Indonesia for the 2011 AFC Cup opener against Sriwijaya F.C., and the club failed to locate him before their departure.

In season 2012, New Radiant faced VB in the first game of the league and Ashfaq managed to score a hat-trick against his former club.

New Radiant also won the President's Cup title after beating Victory Sports Club on penalty shoot-out.

New Radiant packed three points in home and departed to Indonesia on 12 March, for their second match in AFC Cup against Persibo Bojonegoro.

[24] New Radiant was knocked out of the tournament after losing to the champions of 2012 AFC Cup, Kuwait SC from both legs in an aggregate of 12–2.

Throughout the season, Ashfaq scored remarkable 44 goals for the blues and won the best player and top scorer award in that year.

He made his official debut on 21 January in Malaysia FA Cup against KL Spa, scored his first goal for PDRM.

PDRM released Ashfaq on 19 April to participate in AFC Challenge Cup with Maldives national football team.

[29] On 20 June 2014, Ashfaq won the 2014 Malaysia Premier League with PDRM and became the first ever Maldivian player to win a title abroad.

On 20 August, PDRM surprisingly won the second game of the group stage against Malaysian football giants, Selangor in a score-line of 2–0 while Ashfaq scored broke the deadlock from the spot for a foul on him.

[32] PDRM played their first game in POMIS Cup against Ashfaq's previous club, New Radiant, and won the match 1–0.

[35] Ashfaq suffered a hamstring injury in his right leg while playing against Perak on 14 March, returning on 11 April and scoring a goal against Felda United.

On 24 May, Ashfaq announced that he and PDRM had come to an mutual understanding to terminate his contract with 7 months remaining, due to an injury suffered.

In the final minutes of the first half, Ashfaq scored with an brilliant world-class long range shot, which was also praised by the international media as the best goal of the tournament.

Even with the greatest skill of Ashfaq, Maldives lost to Philippines by 3–2 in extra time[47] and had to play third place play-off.

[64] On 24 December, Maldives faced Bhutan in their first game, winning 3–1 with Ashfaq scoring a stunner after beating couple of defenders outside the area.

[citation needed] He is frequently cited as "South Asia's best attacking player", as well as the best Maldivian footballer ever,[70][71][72] and is known for his dribbling ability, agility, speed, skills on the ball, and his powerful, accurate, and clinical shooting, as well as his passing accuracy.

[73] He is famous for rounding goalkeepers and scoring, and is also known for his flair in beating players during one-on-one situations and his ability to penetrate defensive lines.

He is an extremely fast player, with great acceleration and good technical ability, which makes him a threat for opposing defenses during counter-attacks whenever he undertakes individual dribbling runs towards goal, usually starting from the halfway line on either side of the pitch, or even through the centrel his pace also allows him to get on the end of through balls with his runs.

Moreover, he is capable of managing himself effectively in limited spaces, and of attracting defenders only to quickly dash out of the melee or give an assist to a free teammate.

[citation needed] On 15 August 2014, Ashfaq donated one of his football boots to support the Palestine Relief Fund set by Maldivian Red Crescent.