In 1961-62, Caroline Hill finished last in the First Division and were thus relegated. A strong rebound by the club the following year led to a Second Division title and a return to the top flight. However, their success was short lived as the club finished second last in the 1963-64 First Division table and were relegated. After finishing runners up in the 1967-68 Second Division, the club returned to the First Division. Once again, the club finished second last i the First Division and were immediately relegated.
1970's
In 1970-71, the club completed a runners up finish and were promoted back to the top flight. This time however, they stayed there for a decade and enjoyed their greatest run of success. Under the financial support of chairman Chan Yiu Kam, Caroline Hill placed runners up in the 1971-72 First Division, their highest league finish to date. Caroline Hill captured their first major trophy in 1973, defeating Seiko in the Golden Jubilee Cup Final. Four years later, the club once again defeated Seiko, this time in the 1977 Viceroy Cup Final to win their second major trophy. Caroline Hill player Xuan Hudson shared the Best Attacking Player Award in that game with Seiko player Wu Kwok Hung.
1980's
Caroline Hill would return to cup finals in latter years but were unable to come out victorious. In 1980, they lost 2-1 to South China in the Viceroy Cup Final though right winger Deng Jiandong and keeper Liu Chun Fai were voted Best Attacking Player and Best Defending Player respectively. The club suffered heartbreak again the 1981 Viceroy Cup Final, this time losing 7-6 on penalties to Eastern. Liu Chun Fai won his second consecutive Best Defender Award despite the defeat. In 1981-92, mired in a relegation battle with South China, both clubs were involved in a crucial match at South China AA Stadium. Taking place 16 April 1982, a record 27,957 filled the stadium with most arriving early in the morning. The match ended in a 0-0 draw, leaving both teams tied near the bottom of the table with 13 points. South China fans, unhappy with their club's league performance, rioted outside the stadium in the biggest civil disorder in Hong Kong since the 1967 Leftist riots. Desperately sensing the need for improvements to his squad, Chan Yiu Kam turned to England for help. He acquired the likes of Mick Channon, Steve Williams, David Armstrong and Mark Wrighton loan Southampton F.C. in a desperate attempt to help salvage the club's fleeting hopes of remaining in the top flight. However, the home tie versus South China ended in a 4-1 loss, all but sealing their fate. In the end, Caroline Hill finished one point behind them, in 10th place, resulting in relegation to the Second Division.
2000's
In 2001-02, Caroline Hill finished last in the Hong Kong Third A Division League and by rule, were not allowed to enter a team in the Hong Kong Football league the following year. The club has not fielded a senior men's team since.
2010's
Caroline Hill fielded a women's side in the defunct Hong Kong Women League. They currently operate academy sides for youth players.