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He was a member of the South African XV that won the 2019 Rugby World Cup. Playing at right wing, he scored South Africa's second try in the final minutes of the final. Kolbe was nominated for 2019 World Rugby Player of the Year but lost to South Africa teammate Pieter-Steph du Toit.

In June 2019 Kolbe started for Stade Toulousain in the Top 14 final winning the French Championship.

Kolbe made his test debut in 2018 and played a part in Springboks winning the 2019 Rugby Championship. On 2 November, Kolbe was part of the 2019 World-Cup winning team in Japan, scoring a try late in the second half of the Final against England.

Kolbe moved to France to join Top 14 side Toulouse for the 2017–2018 season. Kolbe received a call-up to the South Africa national team for the 2018 Rugby Championship. He made his debut for South Africa against Australia on 8 September, during Round Three of the competition, coming on in the 33rd minute as an injury replacement for Makazole Mapimpi, in a match that South Africa lost 18–23.

He penned a three-year deal to remain at Western Province until 2016.

Kolbe was included in a 12-man squad for the 2016 Summer Olympics in Rio de Janeiro. He was named as a substitute for their first match in Group B of the competition against Spain, with South Africa winning the match 24–0.

Kolbe is a cousin of South African track and field sprinter Wayde van Niekerk, who won the gold medal in the 400 metres at the 2016 Olympics.

In October 2014 he was part of the Western Province team that won the Currie Cup by beating the Lions 19-16.

In 2013, he was included in the training group that toured Argentina in preparation for the 2013 IRB Junior World Championship. He was then included in the squad for the 2013 IRB Junior World Championship.

Between 2012 and 2017, he also represented the South Africa Sevens team. In 2013, he was included in the squad for the 2013 Rugby World Cup Sevens.

He represented Western Province at various youth levels, from the Under-16 Grant Khomo Week in 2009 to the 2012 Under-21 Provincial Championship. He also played for Brackenfell High School at his younger age.

Cheslin Kolbe (born 28 October 1993) is a South African professional rugby union player who currently plays for the South African national team and for Toulouse in the Top 14 in France. His regular position is wing, but he also plays at fullback, He was a member of the South African Sevens team that won a bronze medal at the 2016 Summer Olympics. He was also a member of the Rugby World Cup winning Springboks team at the 2019 Japan tournament