Robben did not make his competitive debut for Chelsea until November 2004, as he was injured in a pre-season friendly match against Roma, breaking a metatarsal bone in his right foot in a challenge from Olivier Dacourt. During this time, he told club doctors that he had noticed an unfamiliar growth on one of his testicles. The medical team quickly did tests to check for testicular cancer, but he was subsequently given the all clear.
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Robben proved to be a crucial player for the 2004–05 season; in November 2004, he was awarded the FA Premier League "Player of the Month" award. Robben ended the 2004–05 season with seven goals, his second highest professional total. He was shortlisted for the PFA Young Player of the Year, but was beaten by Wayne Rooney of Manchester United. Robben was badly injured in a league game away to Blackburn Rovers and forced to sit out Chelsea's title run-in and progress to the semi-finals of the UEFA Champions League. Back to fitness for 2005–06, Robben was an integral part of the Chelsea left wing. In 28 matches, Robben contributed six goals as Chelsea won a second consecutive Premier League championship, the first back-to-back titles for the west London club. Robben and Petr Čech celebrate their second Premier League title in 2006
The 2005–06 season saw Robben involved in an unsporting incident with Liverpool goalkeeper Pepe Reina. Towards the end of a league game between Chelsea and Liverpool at Stamford Bridge, which Chelsea won 2–0, Reina shoved his hand in Robben's face after some provocative words from Robben. Robben fell theatrically to the turf, and Reina received a red card for "violent behaviour", as violent conduct is illegal. As a result of the incident Reina commented that Robben "did well enough to win an Oscar" for his theatrics. Liverpool manager Rafael Benítez later joked in a post-match interview that he "would soon be going to hospital to check on Robben's condition". Reina's red card was not rescinded.
Robben was later named man of the match on 23 December 2006 against Wigan, a match where he got two assists and the winning goal.
Robben with Chelsea
Robben was inflicted with yet another injury in a match against Liverpool on 20 January 2007. Robben made his return in a 3–0 victory against Middlesbrough in February driving in a shot that took a deflection past Mark Schwarzer for an own goal by Abel Xavier. He came on as a substitute for Claude Makélélé in the 2007 League Cup Final against Arsenal and set up the winning goal for Didier Drogba. Robben scored a goal in the second round of the UEFA Champions League against Porto, which led to Chelsea winning the tie 3–2 on aggregate. At the end of March 2007, Robben underwent a knee operation after sustaining a knee injury upon returning from international duty that was expected to rule him out for at least four weeks. He only made two further appearances for Chelsea, both of which were as a substitute and both of which would prove to be key games for the club. His first appearance since returning from injury was against Liverpool in the UEFA Champions League semi final second leg which went to penalties. Robben went on to have his penalty saved by Pepe Reina, and Chelsea ultimately lost. His final appearance for the club came against Manchester United in the 2007 FA Cup Final. Robben replaced Joe Cole at half time, but was then subsequently substituted himself for Ashley Cole in extra time as Chelsea emerged victorious. Spanish club Real Madrid were interested in two of Chelsea's players. Then manager Bernd Schuster is said to have demanded Michael Ballack, while Madrid's former president, Ramón Calderón, was known to favour Robben. Robben said to reporters of Spanish newspaper AS: "I do not know when a deal will be reached. I would like to send a message to the Madrid fans, but I can't until my future is sorted."
Real Madrid eventually secured Robben's services in August 2007. He told Chelsea's official club website: "It was difficult to leave because I had a great time in my three years at Chelsea and I made a lot of friends. There was no time to say goodbye because the deal was closed on the Wednesday at 10 o'clock in the evening and the following morning I had to fly. If I have one day off I would want to come back and say goodbye because to the fans I owe a big thank you because they were always good to me. In my three years I won all the prizes there are to win in England.