In 2008, Cilic reached the semifinals at the Chennai Open, in both singles and doubles. In the singles, he was defeated by Mikhail Youzhny, who went on to win the tournament. Cilic made it to the fourth round of the 2008 Australian Open, taking out two seeds on his way, including 2007 Australian Open finalist Fernando Gonzalez. James Blake beat him in the fourth round. He had achieved his goal for the year of reaching the top 40. His fourth-round result at the Australian Open put him at no. 39 in the ATP rankings.  Cilic also made it to the fourth round of Wimbledon, beating Jarkko Nieminen in five sets in the second round and knocking-out fourteenth seed Paul-Henri Mathieu. At the 2008 Olympics, he reached the second round of the men's singles, beating Juan Monaco before losing to Fernando Gonzalez. He lost in straight sets to Arnaud Clement. At the Canada Masters, he defeated Andy Roddick in reaching the quarterfinal stage, giving his best performance in a Masters Series tournament to date. He lost in three sets to Gilles Simon in the quarterfinals.  Cilic played the Pilot Pen Tennis tournament in New Haven, Connecticut, where he won his first ATP title. He defeated Viktor Troicki, Jurgen Melzer, and Igor Andreev in early rounds, then 2007 finalist Mardy Fish in the final. Cilic, seeded for the first time at a Grand Slam, reached the third round of the US Open, but lost to Novak Djokovic in a match that lasted almost four hours. Cilic came back from a break down in each of the second, third, and fourth sets. In the first round, he had defeated Julien Benneteau in five sets in a match that lasted more than four hours, winning the deciding set.

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