Four of the greatest players to ever step on the tennis court battled in a one-day tournament in Chicago to better their chances of splitting the $1 million prize.

The Champions Series is a New York-based tennis circuit for legendary tennis players over the age of 30.  The series stops at 12 cities and on Oct. 20, the Champions Series made its 10th stop at the United Center, 1901 W. Madison St. The series was created by InsideOut Sports and Entertainment, which is co-owned and operated by Jon Venison and former world No. 1 tennis player Jim Courier.

Courier, 41, who has 23 singles titles under his belt, defeated Andre Agassi in sudden death 7-3. This was his first tournament title since 2009. Courier’s first place finish bumps him up to third place on the Champions Series rankings.

Coming into the Oct. 20 tournament, Agassi was 800 points behind Champions Series rankings leader Pete Sampras. A win would have brought Agassi within 400, but second place is only awarded 200. Semifinalists are awarded 100 points just for participating. First place receive$500,000, second place gets $350,000 and the rest is given to the third place finisher.

The setup of each tournament day is two semifinal matches followed by a championship match between the winners of each semifinal match.

Courier, the co-founder of the Champions Series, started off the tournament when he faced Todd Martin, who has won more than $8 million in prize money, in the first semifinal of the night. Martin, an Illinois native, filled in for injured Bjorn Borg.

“I’m glad [the Champions Series] is willing to bend their criteria to get me in,” Martin said.

Martin had one other appearance in the tournament this year, which was on Sept. 30 in Minneapolis, where he defeated Michael Chang 8-5 in the finals. He failed to duplicate his success this time, losing to Courier, 6-3.

“Today is a great example of why Jim [Courier] was so successful [in his career],” Martin said. “But when it comes down to it, you need to execute, and I didn’t and he did.”

Courier’s game got better as the match went on. Halfway through the semifinal match between Courier and Martin on Oct. 20, it was even at three, until Courier ran away with the match, winning the final three games.

Agassi, 41, who has collected 60 career singles titles during the years, began his day with a 6-4 win over John McEnroe, also a former world No. 1 tennis player, with 77 career titles and more than $12 million in prize money won in his career.

“I made a couple [of] errors with the volley,” McEnroe said. “I could have hit the ball better at the end [of the match].”

Even though the Champions Series is full of some of the greatest tennis legends and matches that have serious implications, the legends had a few laughs with each other on the court. In the finals after scoring on a return, Agassi shouted at Courier, “That shot was the bill payer.”

Agassi and his counterparts had fun at the expense of the ball retrievers. He switched spots with one of the ball girls, allowing her to play a match-point against Courier, who went easy on her, while Agassi played ball boy.

The competitors also engaged fans during the matches when spectators yelled comments at them.

“I never would have thought at this stage we could create a level of entertainment that satisfies the spectators,” Agassi said.