Both have tasted success as port cities and financial centres. But increasingly, the Fragrant Harbour is losing its edge to Singapore in economic development and this has to do with a lack of far-sighted leaders, said a veteran politician who has declared plans to run for the city's top job.
Former security chief Regina Ip, 66, noted that Singapore has invested substantially in high-tech development, going into semiconductors and hard disk drives.
"You encouraged multinationals to do technology transfer and you have the Biopolis. So you managed to diversify your economy," she told The Straits Times in a 30-minute interview on Tuesday. "I think we compare very poorly with Singapore in terms of leadership and economic policy."
Calling herself half-Singaporean, as her father was a Singaporean-Chinese businessman, Mrs Ip said she is a "great admirer" of Singapore founding prime minister Lee Kuan Yew. She said she had dined with him twice and was inspired by him.
"Singapore benefits from very strong and able leadership - far-sighted leadership, which is something we don't have," she said.
Mrs Ip, who used to be Director-General of Industry, said unlike Singapore, Hong Kong does not have a focused industrial policy.
"Our Financial Secretary's talk of food trucks - it's a joke," she said, taking aim at an initiative by potential election rival John Tsang, who had first suggested operating food trucks at tourist spots last year.
The co-founder of pro-Beijing New People's Party is only the second person to declare her candidacy for the March 26 polls, after retired judge Woo Kwok Hing, 70.
Chief Secretary Carrie Lam and Mr Tsang are widely expected to run. But analysts say Mr Tsang's candidacy depends on whether Beijing accepts his resignation, which was submitted about two weeks ago.
Another possible contender is former Legislative Council (Legco) president Jasper Tsang, who said he would wait and see before nomination closes on March 1.
Hong Kong will get a new top leader, to be chosen by a committee of 1,194 people, after incumbent Leung Chun Ying declared that he would not try for a second term.
Of the city's two former chief executives Tung Chee Hwa and Donald Tsang, and the current Chief Executive, Mrs Ip felt that only Mr Tung can be considered far-sighted.
"Mr Tung wanted to push (for) technology and development. Unfortunately, the timing was not good for him. He took office soon after the Asian financial crisis and the dot.com collapse in the United States," she said.
Mr Donald Tsang, a former civil servant, and Mr Leung, former chairman of property firm DTZ Debenham Tie Leung Asia, "lack the vision of Mr Tung or Mr Lee", said Mrs Ip, the first female Secretary for Security.
But Mrs Ip, who kicked off her campaign on Dec 15 with the slogan "Win Back Hong Kong", drew a lot of vitriol in 2003 when she pushed for Basic Law Article 23, which bans acts of treason and subversion against the Chinese government.
During her campaign earlier this month, she said she aimed to revive Article 23. She immediately became a target of criticism. But she said she is not disturbed by the harsh criticism and her popularity is evident - she was thrice elected into the Legco and crowned "queen of votes" as the female candidate with the most votes in the September polls.
"I am actually a compassionate person who takes good care of people who work for me. I am well-known in the civil service for being a good boss," said the widow, who has a 27-year-old daughter.
Mrs Ip, who has vowed to fix housing, social and economic problems if elected, conceded that Hong Kong is now highly polarised, attributing this to the rise of anti-establishment and anti-elite sentiments around the world. "The main political cleavage is actually the attitude towards China," said Mrs Ip. She said she hopes to "heal the rift" by promoting a greater understanding of Chinese history and culture in schools.