From 1996 to 1998, the Crew played its home games at Ohio Stadium on the campus of Ohio State University. Although the Crew enjoyed success during their tenure there, the large seating capacity and limitations to the field size made the stadium ill-suited for soccer. In 1999, the Crew moved into Columbus Crew Stadium (later renamed Historic Crew Stadium), the first soccer-specific stadium built by a Major League Soccer team.

Kyle Martino left the University of Virginia after his junior season, signing a Project-40 contract with Major League Soccer and entering the 2002 MLS Superdraft, where the Columbus Crew selected him eighth overall. He tallied 2 goals and 5 assists in 22 appearances and won the MLS Rookie of the Year Award, while running the Crew offense for much of the season.

The Crew won its first MLS Cup in 2008, led by Guillermo Barros Schelotto, who scored seven goals and had 19 assists and won the MLS Most Valuable Player Award. The team also won its second Supporters' Shield, going 17-7-6 in the regular season, and winning playoff games against Sporting Kansas City and the Chicago Fire before beating the New York Red Bulls 3-1 in the final.

Mars' Snickers chocolate bar was the Crew's first uniform sponsor, on a five-year, $6 million deal that lasted from 1996 to 2000.

Former teen phenom Eddie Gaven did everything--score, assist, defend, and especially hustle. He also propelled the Crew to their first MLS Cup Final with a game-winning goal in the 2008 Eastern Conference Championship game. The Crew went on to win the Final.

Never a big scorer, Robin Fraser only scored one regular season and one playoff goal in his entire MLS career. He played for the Crew in 2004 and 2005, making a total of 56 appearances, without a single goal or assist.

Despite a contract clause that dictated he play for his hometown Los Angeles Galaxy, MLS allocated Paul Caligiuri to Columbus in 1996. Although he did score 3 goals for the Crew, Caligiuri sued Major League Soccer over the issue, and in March 1997 was placed with LA Galaxy, despite his high salary and the fact that the Galaxy were close to the salary cap.

McBride played his final season with Columbus in 2003 before joining Fulham of the Premier League.

Despite winning the MLS Coach of the Year Award in 2004, Andrulis was fired in July 2005 and replaced on an interim basis by Robert Warzycha. After missing the playoffs, the club hired former L.A. Galaxy and UCLA head coach Sigi Schmid for the full-time position. Warzycha spent several years as Schmid's assistant before being promoted to head coach himself in 2009 and holding the position for five seasons.

The Crew played their first game on April 13, 1996, in front of a home crowd of 25,266 in Ohio Stadium against D.C. United and won 4-0.