Chinese Super League side Shanghai Shenhua slumped out of the AFC Champions League after a goalless draw against Japan's ten-man Urawa Red Diamonds on Wednesday.

Shenhua, quarter-finalists last year, picked up their first point in four games but it wasn't enough to keep them in the continental competition. They needed to win to stand any chance of reaching the knockout phase.

Group E leaders Urawa dropped their first points of the campaign after three wins from three, but nearly sneaked victory in the dying minutes when Makoto Hasebe's diving header was kept out by a fine save from Wang Dalei.

The J-League champions were the better side but failed to break the deadlock. Yuki Abe had their best chance, hitting the crossbar in the first half. At the other end, Shanghai captain Jiang Kun blazed over early on and Liu Zhiqing squandered an opportunity in the seventh minute, heading over from six yards out after a low cross from Xie Hui eluded Urawa goalkeeper Ryota Tsuzuki.

Urawa were reduced to ten men for the final 15 minutes after skipper Nobuhisa Yamada was sent off by Omani referee Mahmood Al Ghatrifi for apparent time wasting.