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Cheng joined Eastern in 2013 and made 26 appearances for the club. He retired from football in 2017 with his final match coming in Eastern's 3-0 win over Southern in the 2016-17 season playoff.

In the league, on 21 February 2011, Cheng Siu Wai scored in the 87th minute to help Kitchee beat Tai Po FC 2:1 to stay ahead of South China. Kitchee eventually beat South China to win the 2010–11 league title.

Cheng Siu Wai signed to play for Sun Hei SC on 27 June 2011. Cheng said he has won numerous trophies in the past but never any individual awards. In the new season he hopes to win an individual award. He scored his first goal for Sun Hei on 17 September 2011 in a 2:1 win away to Tuen Mun SA. On 16 October 2011, Cheng Siu Wai became the first player to score a goal at the newly renovated Mong Kok Stadium, in a 5–0 win against Sham Shui Po SA. On 22 October, Cheng Siu Wai scored the winning goal against Biu Chun Rangers, just 1 minute from the end, to secure a 1–0 win. On 27 November, Cheng Siu Wai scored a goal against Tai Po FC in the 2011–12 Hong Kong Senior Challenge Shield quarter-final second leg match and was named Player of the month for October.

He has been capped 11 times at international level for Hong Kong, and he has scored 7 goals. One of them a diving header against Bahrain in the 2011 AFC Asian Cup qualifier. It was the only goal Hong Kong managed in six qualification matches. In December 2011, Cheng Siu Wai was recalled to the Hong Kong team after consistent good performances for Sun Hei SC, to play in the 2012 Guangdong-Hong Kong Cup. He scored with a header from a Jack Sealy pass in the first leg and the match ended 2–2.

On 9 May 2010, Cheng Siu Wai scored two goals and helped Kitchee beat Happy Valley 6:0. On 31 May 2010, Cheng Siu-wai scored the equaliser for Kitchee against Beijing Guoan Talents in the 2010 Singapore Cup, forcing extra time which Kitchee won 2:1 in the end.

When Cheng Siu Wai first joined South China, his monthly salary was only HK$4,000 (approx US$500). By the time he left in 2008, it went up to HK$11,000 (approx US$1,375). Because of his difficult financial situation, he lived in the club's quarters and only returned home once a week.

On 11 March 2008, Cheng Siu-wai scored two goals for South China against Home United FC of Singapore, at Mongkok Stadium in an AFC Cup group game. However, South China lost in the end by 2–3.

Cheng Siu Wai moved to TSW Pegasus FC when the club was formed at the end of 2008. He was named the club's captain. Cheng claimed he moved to get more playing time. Cheng scored against South China AA in the 2008–09 Hong Kong Senior Challenge Shield Cheng claimed beating South China was one of the teams' targets and he was very happy with the goal and victory. The club went on to win the tournament by beating Sun Hei SC 3:0 in the final. But after just one season at the club, he was loaned to Kitchee.

Despite his resemblance to Thierry Henry, his favourite player is David Beckham, after meeting him in an exhibition match between South China AA and Los Angeles Galaxy in 2008.

He was a member of the squad that got South China relegated at the end of the 2005–06 Hong Kong First Division League season. But the club was retained in the first division upon Steven Lo's appointment as the club's convener.

Cheng Siu Wai was released by Buler Rangers one month before the end of the 2004–05 Hong Kong First Division League season because he failed to reach the club's expectations.

Cheng Siu Wai made his Hong Kong First Division League debut in 2002 with Double Flower. He scored his first goal on the same day with a volley at Mong Kok Stadium.

Cheng Siu Wai (Chinese: 鄭少偉 ; Cantonese Yale: Jehng Siuwáih , born 27 December 1981, Hong Kong) is a former Hong Kong professional footballer player whose position was striker. His shirt name was Henry.