Qatar's Al Rayyan crashed out of the Asian Champions League after being handed a heartbreaking 4-3 defeat by Saudi giants Al Hilal on Monday.
The Michael Laudrup managed side needed a win to secure their first ever last 16 berth but a brace each by Nicolas Milesi and Omar Khribin in a Doha thriller put paid to their hopes as already qualified Al Hilal went on to top Group D with 12 points from six matches.
Iran's Persepolis made the last 16 as the second placed side in the group with nine points after defeating the UAE's Al Wahda 4-2 thanks to a hat-trick by international Mehedi Taremi.
Taremi struck in the 20th, 54th and 70th minutes to add to Souroush Rafiei's 17th minute goal, while Al Wahda, who had only the slimmest of chances to qualify, could only score two with Ahmed al-Akberi and Sebastian Tagliabue on target.
With only Al Hlial's spot in the knockouts secure in Group D, both Al Rayyan and Persepolis needed victories to ensure their progress but it was the Iranians who proved lucky on a day which saw 13 goals scored in the two Group D matches.
Al Hilal, who had also won their previous clash with Al Rayyan, went ahead in the 40th minute when Uruguayan Milesi knocked the ball in off a rebound from a failed earlier attempt by Nawaf al-Abid.
But Al Rayyan stormed back in stunning fashion in the 55th minute thanks to captain Rodrigo Tabata's defence splitting run down the middle culminating in a brilliant finish from Sebsatian Soria.
Tabata, one of the many naturalized South American born stars playing for the Qatar national team, then helped Al Rayyan go ahead with another great piece of individual brilliance in the 59th minute.
Receiving the ball from a throw-in on the right, the versatile midfielder executed a measured left-footed chip from far that left the Al Hilal goalkeeper Abdulla al-Maiouf completely flummoxed.
- Tempers fray -
Al Hilal equalized through Khribin in the 66th minute and then took a 3-2 lead in the 73rd with Milesi netting his second goal from just outside the box with a powerful shot to the top right corner of the net.
Al Rayyan, however, were not finished yet and as tempers frayed former Barcelona player Sergio Garcia made good on an assist by Tabata to fire past al-Maiouf in the 82nd minute to draw level.
Al Hilal, however, grabbed the winner just two minutes later with Khribin following a headed pass by Mohamed Jahfali after a corner.
In Group C Saudi Arabia's Al Ahli confirmed their place in the knockout phase as they handed Iran's Zobahan a 2-0 defeat.
The Jeddah-based club took all three points to secure second place and set up a last 16 meeting with the winners of Group A, which will be determined on Tuesday.
After a goalless first-half, Abdulfattah Asiri gave Al Ahli the lead in the 63rd minute and, with six minutes remaining, Amiri Kurdi put the result beyond a doubt when he slid in to score from six yards out.
UAE giants Al Ahli had already qualified but they ensured they topped the group with a 3-0 win over Bunyodkor of Uzbekistan.
Omar Abdulrahman scored one goal and contributed in the other two at the Hazza bin Zayed Stadium in Al Ain.
Nassir al-Shamrani scored with a low shot to put the hosts ahead from an Abdulrahman pass in the 34th minute.
Abdulrahman then added his name to the scoresheet with a well-struck free-kick in the 77th minute before Ibrahim Diaky rounded off the win in injury time by heading home an Abdulrahman corner in stoppage time.
© 2017 AFP