It actually never expected a humdrum year as the grouping of 10 South-east Asian nations was set to sign a charter that would change its status to a legal entity with rights and obligations and put it on course for greater integration.
Singapore was supposed to manage that transition in its year as the chairman.
But as it turned out, Singapore found itself doing much more than that as the grouping was swept up by two crises, both involving member-state Myanmar.
The first to hit was the bloody crackdown on demonstrations in Yangon by the military regime last September, barely two months after Singapore took over the chairmanship.
The Asean foreign ministers, who were attending the United Nations General Assembly in New York, met in an emergency session.
They issued a strong statement condemning the crackdown that 'took many people, including ourselves, by surprise', recounted Foreign Minister George Yeo during an interview this week.
After that, UN special envoy Ibrahim Gambari visited Myanmar to help bring about national reconciliation.
As for Asean, 'we were very anxious that a process of national reconciliation in Myanmar should begin with the encouragement of the entire Asean family', noted Mr Yeo.
Singapore, as the chairman, invited Professor Gambari to the Asean summit in the Republic last November. But Myanmar did not agree to Asean leaders meeting the UN special envoy.
'Till today, I don't understand why Myanmar thought that it was better off dealing directly with the UN than with the UN through Asean,' said Mr Yeo. 'We offered our hands of friendship. The offer was declined.'
For him, that was a low point of Singapore's leadership of Asean.
In any case, the UN process was interrupted by Cyclone Nargis, 'a terrible disaster of biblical proportions' that killed tens of thousands of people. That led to a stand-off between a suspicious Myanmar government and a global community ready to render aid but was instead kept at bay.
Asean received a great deal of flak initially for not responding quickly enough to the cyclone and to the stand-off.
But at an informal meeting in May, Asean foreign ministers confronted their Myanmar counterpart and asked him point-blank 'what Asean meant to Myanmar'.
The ministers then agreed to establish a mechanism to help Myanmar, a tripartite group consisting of teams from Asean, the UN and Myanmar to manage the relief efforts so that international aid could reach the devastated areas.
This, for Mr Yeo, was the high point for Singapore.
One of the highlights of the year was the completion of the Asean Charter despite hiccups along the way. It was signed last November.
In all, 'it's been a long year, quite an eventful one year under Singapore's chairmanship', said Mr Yeo.
One key lesson that Singapore should take from this year is 'to be prepared for the unexpected', noted Asean expert Yeo Lay Hwee of the Singapore Institute of International Affairs.
Going forward, Singapore must work hard to keep Asean focused on economic cooperation and on its external engagement, she added.
Singapore hands over the rotational chair to Thailand at the Asean Ministerial Meeting next week.
GOH SUI NOI