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Freeman was selected for Liberia under-20 team for the 2018 WAFU/FOX U-20 Tournament. He made his debut in Liberia opening game against Ivory Coast which ended with a 3–0 defeat for Liberia. In the second game against Guinea Bissau, he scored his first goal for Liberia U20 to help the team win 2–1. He went on scoring a goal in the quarterfinals against Sierra Leone to help Liberia win 5–1. He ended the tournament with two goals and three assists as Liberia finished as runners-up behind champions Gambia.

His hard work on and off the pitch with Swankamore Football Club and Nimba County in the Liberian National County Meet did not go unnoticed as he became the target of several top clubs in Liberia. Freeman was chased by clubs including Invincible Eleven, FC Fassell and Barrack Young Controllers FC II. He ended all speculations by joining Watanga FC on a three-year and half year deal. He joined the club before the start of the second phase of the 2016-17 Liberian Premier League. Freeman proved to be one of the best young talents in the country in his debut year with Watanga FC by scoring five goals in six games. He went on playing two full season with the club before moving to Israel to sign for Hapoel Ramat Gan Givatayim F.C..

Born in Monrovia, Liberia, Chauncy Freeman started playing football in his local community, Swankamore Community. His hard work and dedication to football quickly helped him become a better footballer. He began his football journey with third division, Todd Football Club in 2013. He spent a year with the team and join his community club, Swankamore Football Club. He spent two years with the club and help them reach the third division regional playoffs. During his two years with Swankamore Football Club, he played for Nimba County in the Liberian National County Meet. He was part of the Nimba County football team that qualify from the 2015-16 Liberian National County Meet group stage.

Chauncy B. Freeman (born 26 July 2001), is a Liberian footballer who plays as a striker for the U-19 team of Israeli Premier League club Hapoel Ramat Gan Givatayim F.C..