Professional baseball in Cleveland is one of the city's oldest traditions, dating back to 1869. There is a passionate connection between the city of Cleveland and the Indians, as they are a study in revival. Both are working, living examples of the power of teamwork, conviction and dedication.

In 1994, the ballpark opened under the name Jacobs Field as the new home of the Cleveland Indians, which had previously shared Cleveland Municipal Stadium with the NFL's Cleveland Browns.

In May 1990, Cuyahoga County voters approved a 15-year sin tax on alcohol and cigarette sales in order to finance the new sports complex. In June 1992, the ceremonial first pitch was thrown at the site of the new Jacobs Field before construction of the building began. On April 4, 1994, the Indians played their first game at the new stadium. President Bill Clinton threw out the ceremonial first pitch, and the Indians defeated the Seattle Mariners 4-3 in 11 innings.

In 1995, it hosted its first World Series, which the Cleveland Indians lost to the Atlanta Braves, and two years later was the site of the 1997 MLB All-Star Game and the host of the 1997 World Series, which the Cleveland Indians lost to the Florida Marlins.

Prior to the start of the 1997 season, two sections of seating were added onto the ends of the bleacher section, increasing the capacity by about 1,000 to its current 43,345.

In 2004, its scoreboard, the largest free-standing scoreboard in the United States, was modernized with the installation of the largest video display in the world at a sports venue, built by Daktronics of South Dakota. The video board measures 36 feet high by 149 feet wide. Also in 2004, a center field dining area located behind the seating, formerly occupied by auxiliary bleachers, was replaced with a bar area called the Batter's Eye Bar.

In 2007, the Cleveland Indians opened Heritage Park, a section honoring the Cleveland Indians Hall of Fame, the 100 greatest Cleveland Indians players, memorable Indians moments, and a memorial plaque for Ray Chapman that was originally installed in League Park. It is located behind the center field wall, shielded by plantings so it doesn't interfere with the batter's eye.

On October 5, 2007, in the eighth inning of a playoff game against the New York Yankees, a swarm of insects (believed to be midges from Lake Erie) enveloped the playing field, distracting relief pitcher Joba Chamberlain. Chamberlain walked Grady Sizemore who later scored the tying run on a wild pitch. The incident became known as the "Bug Game."

Originally named for former team owners the Jacobs brothers, the original naming rights expired at the end of 2006.

On January 11, 2008, it was announced that naming rights to the park had been bought by Progressive Corporation, an insurance company headquartered in nearby Mayfield Village, the original naming rights having expired at the end of 2006. Removal of the iconic Jacobs Field sign on the front of the building began the morning of January 18, 2008, with the replacement sign installed on March 25, 2008. Progressive agreed to pay $57.6 million for the naming rights for 16 years.