On February 21, 2008, Szczerbiak and West were traded by the SuperSonics to the Cleveland Cavaliers in a three-way deal involving the Chicago Bulls that sent Ira Newble and Donyell Marshall from Cleveland to Seattle, Adrian Griffin from Chicago to Seattle, Cedric Simmons, Drew Gooden, Larry Hughes, and Shannon Brown, from Cleveland to Chicago, and Ben Wallace and Joe Smith from Chicago to Cleveland.

Szczerbiak played in 25 regular season games (one start) with the Cavaliers averaging 8.2 points and 3.2 rebounds.
He scored 18 points against Detroit on April 16, 2008.
Between the SuperSonics and the Cavaliers, Szczerbiak played in 75 games (two starts) and averaged 11.5 points and 2.9 rebounds.

During the 2008 NBA Playoffs Szczerbiak started at shooting guard for the Cavaliers, helping the Cavs defeat the Washington Wizards in the first-round by putting up 26 points and shooting 6–13 from the 3 point line in game six.
For the playoffs, Szczerbiak averaged 10.8 points per game.

During the 2008–2009 NBA season, Szczerbiak played in 74 games, starting in 5 of them.
Given 20 minutes a game, Szczerbiak averaged 7 points, 3.2 rebounds, and 1.1 assists while shooting .450% from the field and .411% from the 3-point line.
On February 21, 2008, Szczerbiak and West were traded by the SuperSonics to the Cleveland Cavaliers in a three-way deal involving the Chicago Bulls that sent Ira Newble and Donyell Marshall from Cleveland to Seattle, Adrian Griffin from Chicago to Seattle, Cedric Simmons, Drew Gooden, Larry Hughes, and Shannon Brown, from Cleveland to Chicago, and Ben Wallace and Joe Smith from Chicago to Cleveland.
Szczerbiak played in 25 regular season games (one start) with the Cavaliers averaging 8.2 points and 3.2 rebounds. He scored 18 points against Detroit on April 16, 2008. Between the SuperSonics and the Cavaliers, Szczerbiak played in 75 games (two starts) and averaged 11.5 points and 2.9 rebounds.
During the 2008 NBA Playoffs Szczerbiak started at shooting guard for the Cavaliers, helping the Cavs defeat the Washington Wizards in the first-round by putting up 26 points and shooting 6–13 from the 3 point line in game six. For the playoffs, Szczerbiak averaged 10.8 points per game.
During the 2008–2009 NBA season, Szczerbiak played in 74 games, starting in 5 of them. Given 20 minutes a game, Szczerbiak averaged 7 points, 3.2 rebounds, and 1.1 assists while shooting .450% from the field and .411% from the 3-point line.
Wally Szczerbiak