Chan Yuen-ting became the first woman to lead a men's team in a continental competition against Guangzhou Evergrande Taobao, but the occasion was soured as her Eastern team were thumped 7-0.
Eastern - the first team from Hong Kong to play in the AFC Champions League - were humiliated in China as they ended the match having been reduced to nine men.
Hosts Guangzhou, managed by Luiz Felipe Scolari, recorded 38 shots - 18 of which were on target - while their opponents failed to find the target with either of their two attempts.
Eastern got off to a nightmare start when Wong Tsz Ho was sent off in the third minute for hand ball in the penalty area, with Ricardo Goulart scoring the resulting spot-kick.
It was already 3-0 by the time Wong Chi-Chung was sent off for a second yellow card in the 34th minute, leaving the history-making Chan with the most difficult of tasks.
Ultimately, winger Liao Lisheng and defender Wang Shangyuan scored doubles, while Paulinho and Alan also got on the scoresheet.
Alan even had time to miss a penalty, conceded due to another handball that resulted in the first of Wong's two bookings.
RAMIRES TO THE RESCUE
Jiangsu Suning opened their group-stage campaign with a dramatic 1-0 victory away to Jeju United, courtesy of a last-minute strike from Ramires.
The former Chelsea midfielder found the bottom corner after a long free-kick was not dealt with by the home defence.
Jeju were unfortunate to come away from the match with nothing after Lee Chang-min hit the post in the first half and Marcelo Toscano struck the woodwork in the second.
AWFUL ADELAIDE SEASON GOES ON
Adelaide United's defence of their A-League title has been terrible – they sit bottom of the table after 20 matches – and their Champions League campaign began on a similarly low note.
They were thrashed 3-0 by Gamba Osaka at Hindmarsh Stadium in a repeat of the 2008 final, one which also saw the team from Japan emerge victorious.
Shun Nagasawa's header put Osaka ahead, before Yasuyuki Konno's high finish in first-half stoppage-time served as a hammer blow.
Dylan McGowan's own goal with nine minutes remaining ended the scoring as Adelaide only mustered one shot on target in the match.
Wednesday's other game saw Kawasaki Frontale draw 1-1 at home to two-time winners Suwon Bluewings.
Both goals came inside the first 23 minutes, with Shogo Taniguchi's own goal cancelling out captain Yu Kobayashi's early close-range strike.
