MANCHESTER, England (AP) — Few matches will have been more painful for Manchester United midfielder Ryan Giggs than his 1,000th as a pro on Tuesday.

After being selected to start against Real Madrid to reach the milestone, the 39-year-old Giggs turned in an impressive, age-defying display before seeing his team crumble in the second half and exit the Champions League.

Giggs had been at the heart of United's attacking impetus in the first half, bursting across the pitch and delivering balls with precision to setup goal-scoring opportunities.

But after United did finally go in front — through Sergio Ramos' own goal at the start of the second half — the buoyant mood was quickly deflated inside Old Trafford.

A red card for Nani for a studs-up, flying challenge on Alvaro Arbeloa, saw United reduced to ten men in the 56th minute.

Ten minutes later, Madrid was level through Luka Modric's curling strike off the post. And Cristiano Ronaldo netted inside three minutes to shatter the European dreams of his former club by sending Madrid through with a 2-1 second-leg win after drawing 1-1 at home.

At the final whistle, as the United fans jeered the referee who sent off Nani, even the usually placid Giggs was pointing in anger at Cuneyt Caki.

Now Giggs' hopes of adding to his two Champions League successes will have to wait another season.

Like the rest of his team, Giggs was prevented from speaking to the media after the match, with assistant manager Mike Phelan issuing the only public reaction to a night that enraged the hosts.

Phelan said Giggs' landmark match and a "great performance was marred by one decision" by the referee.

"The players sensed they were in control and then it drifted away," Phelan said.

Now the focus shifts to advancing in the FA Cup by beating Chelsea on Sunday.

And Giggs seems certain to collect a 13th Premier League winners' medal this season, with United currently 12 points ahead in title race.

Tuesday's match was Giggs' 932nd match for United, where he has spent his entire career since making his debut in 1991. Giggs has also played 64 times for Wales and made four appearances for Britain at last year's London Olympics.