At Wimbledon 2009, he powered through the first two rounds, beating Lukáš Lacko and Steve Darcis.
In the next two rounds he needed only one break of serve in the third set to defeat both ninth seed Jo-Wilfried Tsonga and seventh seed Fernando Verdasco, advancing to face Roger Federer in his first quarterfinal at a Grand Slam.
The match was a relatively one-sided affair, with Federer winning in straight sets and going on to win the tournament.

In the 2009 Davis Cup semifinals, Karlović was defeated by Radek Štěpánek, despite hitting a record-breaking 78 aces (the record has since been taken by John Isner).
The match was one of the longest in the history of the Davis Cup, lasting 5 hours, 59 minutes.
There were only three breaks of serve in this match.

Karlović also won his first five-set match in the Davis Cup quarterfinals against the United States, where he came from behind to beat James Blake from two sets down.
At Wimbledon 2009, he powered through the first two rounds, beating Lukáš Lacko and Steve Darcis. In the next two rounds he needed only one break of serve in the third set to defeat both ninth seed Jo-Wilfried Tsonga and seventh seed Fernando Verdasco, advancing to face Roger Federer in his first quarterfinal at a Grand Slam. The match was a relatively one-sided affair, with Federer winning in straight sets and going on to win the tournament.
In the 2009 Davis Cup semifinals, Karlović was defeated by Radek Štěpánek, despite hitting a record-breaking 78 aces (the record has since been taken by John Isner). The match was one of the longest in the history of the Davis Cup, lasting 5 hours, 59 minutes. There were only three breaks of serve in this match.
Karlović also won his first five-set match in the Davis Cup quarterfinals against the United States, where he came from behind to beat James Blake from two sets down.
Ivo Karlović