LEIPZIG, Germany (AP) – Angola’s first World Cup goal wasn’t nearly enough to send the Black Antelopes into the second round of the tournament.

Sohrab Bakhtiarizadeh scored the tying goal in the 75th minute Wednesday to give Iran a 1-1 draw and end Angola’s hopes of advancing at its first World Cup ever.

Needing a win, a Mexico loss to Portugal and help on goal differential to move on, the Angolans couldn’t deliver the one part they controlled.

They finished in third place in Group D with two points, one ahead of Iran.

Substitute Flavio gave Angola its first goal of the tournament when he broke free from Kaabi Hossein in the penalty box to head a cross from Ze Kalanga over goalkeeper Ebrahim Mirzapour and into the net.

Angola lost 1-0 to Portugal in its opener before playing Mexico to a 0-0 draw.

Iran tied it 15 minutes later when Bakhtiarizadeh jumped over Love and headed a corner kick from Mehdi Mahdavikia just inside the post with no defenders guarding the area. Goalkeeper Joao Ricardo yelled at his defenders after the score in apparent frustration.

With Mexico losing 2-1 to Portugal, Angola would have needed three goals in the closing minutes to advance.

But the Black Antelopes showed little urgency, apparently satisfied with their second draw of the tournament.

It was an outcome that neither side had wished for.

The Iranians, who generated security headaches for the hosts because of protests against the government in Tehran, had already been eliminated after losing their two matches in the group.

But they remained hopeful they could return home “honorably” by beating Angola.

After a scrappy beginning, Iran generally dominated the first half, mounting a series of ineffective attacks which tested Angola’s solid defense.

Still, the Black Antelopes had the first real opportunity in the 12th minute with Mateus shooting over the crossbar from inside the penalty area.

Iran replied two minutes later when Ricardo smothered a low shot from Kaiserslautern’s Ferydoon Zandi. Ricardo stopped a free kick by Ali Daei in the 24th from the edge of the area, whose return header from close in went over the bar.

Iran’s best chance came in the 27th minute, when defender Mendonca stopped Zandi’s header in the goalmouth.

Angola coach Luis Oliveira Goncalves made only one change in the team that had displayed a strong and disciplined defense in its two previous Group D matches but had scored no goals. Still, the Africans played much more openly than in the first two games and mounted repeated forays toward Mirzapour’s goal.

Iran coach Branko Ivankovic dropped the team’s biggest star, Bayern Munich playmaker Ali Karimi, from the squad because of his poor form and erratic behavior. He was replaced by the 37-year old Daei, who had likely played his last match for the national team.

Ivankovic had hoped for a “home advantage” at the match, counting on the 200,000 Iranian residents in Germany to turn out in force. But Iran’s fans appeared to be outnumbered by Angola’s supporters waving their red-and-black banners.

AP-ES-06-21-06 1213EDT