[5] Born in Fort Wayne, Indiana, Beasley joined IMG Academy, the United States Soccer Federation's Residency program in Bradenton, Florida.

Beasley starred in the 1999 Under-17 World Cup in New Zealand, winning the Silver Ball as the tournament's second best player, behind teammate Landon Donovan.

[7] His stay with the Fire ended on July 19, 2004, when Dutch giants PSV Eindhoven agreed on a transfer fee with MLS worth $2.5 million.

In addition to making an impact on the domestic level, Beasley became the first American to play in the semi-finals of the UEFA Champions League, against Milan.

[10] After a disappointing individual season for Beasley in which PSV won their 19th championship, on August 31, 2006, he joined English Premier League side Manchester City on a season-long loan fulfilling his ambition to play in England.

On August 4, 2007, Beasley made his Rangers debut, playing a full 90 minutes in a 3–0 win against Inverness Caledonian Thistle.

During the match, Beasley was subjected to racial taunting by Zeta fans, along with fellow black teammate, Jean-Claude Darcheville.

Beasley's wide pass to Alan Hutton allowed him to spring free and set up Daniel Cousin for the second.

[18] During a Champions League match against VfB Stuttgart, Beasley was hurt in a collision with goalkeeper Raphael Schäfer.

His first start for Rangers after his injury came in the Scottish Cup final against Queen of the South; he notched a goal and an assist in the 3–2 victory.

[21] Beasley helped Rangers win the SPL title for 2008–09, being awarded a championship medal after appearing in ten league matches during the season.

After the Motherwell game Beasley expressed his desire to stay with Rangers and help them retain the Scottish Premier League title.

[25] On July 23, Beasley made his competitive debut for Los Camoteros in a 1–0 win over Atlas in the opening match of the 2011 Apertura Season.

[27] On July 23, 2014, Beasley joined Major League Soccer club Houston Dynamo as a designated player.

[32] He received the MLS Fair Play Individual Award, which is given to the player who commits the fewest fouls and demonstrates good sportsmanship.

Beasley scored the only goal of the match hitting a weak foot volley from outside the box to give the Dynamo the win.

After the match the Dynamo showed a tribute on the videoboard and Beasley addressed the crowd, saying "I wouldn't think of another club to end my career with.

At age 20, he was named in the United States' squad for the 2002 World Cup in Japan and South Korea, playing in all three group matches as the team achieved its best performance in over half a century by reaching the quarter-finals.

Beasley, along with fellow young midfielder Landon Donovan, was criticized by fans and U.S. coach Bruce Arena for poor play during the 2006 World Cup.

In a 2010 World Cup qualification fourth-round game against Trinidad and Tobago, Beasley played the full 90 minutes at left back.

Beasley was named by U.S. coach Bob Bradley to the nation's 23-man roster for the 2010 World Cup, but made only one substitute appearance in a group stage match, against Algeria.

He started at left back and received strong reviews in a victories over Costa Rica, Jamaica, Panama, and a draw against Mexico.

[44] In July 2013, United States national team manager Jürgen Klinsmann named Beasley captain for the 2013 CONCACAF Gold Cup, where he started at left-back for five of the six matches the U.S. played.

[54] On October 28, 2020, Fort Wayne FC announced Beasley's addition to their ownership group as co-owner of the club.