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On 28 June 2019, Kapanen signed a new three-year, $9.6 million contract with Toronto worth an annual average value of $3.2 million.

After attending the Maple Leafs' training camp, Kapanen began the 2018–19 season NHL. As teammate William Nylander remained unsigned and in contract negotiations with Toronto, Kapanen replaced his spot on the team's top line. Kapanen finished the season with 20 goals and 44 points in 78 games.

Kapanen returned to the Marlies the following season and quickly became one of their best players. Despite periods of injury, he scored at a pace of a point-a-game before an injury to Maple Leafs forward Nikita Soshnikov resulted in Kapanen being recalled to the Maple Leafs late in the season. Kapanen took a role on the fourth line alongside Brian Boyle and Matt Martin, playing well in limited minutes. He scored his first NHL goal on 8 April 2017 against the Penguins, the team that had drafted him. The goal was a vital one in a game that saw the team clinch a spot in the Stanley Cup playoffs for the first time since 2013, a remarkable feat considering the Maple Leafs finished last in the entire league the previous season. A week later, he scored with 8:07 left in double overtime in Game 2 of the Eastern Conference Quarterfinals as his Maple Leafs defeated the Washington Capitals 4–3 to tie the series at one game apiece. The Leafs ended up losing the series in six games.

Kapanen was sent down to the Marlies to begin the 2017–18 season, but was recalled on 28 October 2017 after playing six games for the Marlies. He was sent back down to the Marlies on 7 November, only to be recalled again on 12 December. He had been selected for the 2018 AHL All-Star Game, but was replaced by Andreas Johnsson. Kapanen recorded his first and only goal of the 2018 playoffs in Game 7 against the Boston Bruins, becoming the youngest player in NHL history to score a shorthanded goal in a Game 7. The Maple Leafs lost the series 3–4. Following the Maple Leafs' defeat, Kapanen joined the Finland senior national team at the 2018 IIHF World Championship.

At the 2016 World Junior Ice Hockey Championship, Kapanen scored the game-winning goal in overtime against Russia to win the gold medal.

Kapanen began the 2015–16 season with the Maple Leafs' American Hockey League (AHL) affiliate, the Toronto Marlies. As the youngest player in the AHL, Kapanen played well in his role on a deep Marlies team that finished first in league standings. He made his NHL debut on 29 February 2016 against the Tampa Bay Lightning as part of a night where four players would make their debut, including William Nylander. Kapanen would play nine games for the struggling Maple Leafs, recording no points before being returned to the Marlies for the team's 2016 Calder Cup playoff run. Despite finishing as the top seed, the Marlies were eliminated in the Eastern Conference Finals by the Hershey Bears.

On 1 July 2015, Kapanen was traded to the Toronto Maple Leafs in a blockbuster, multi-player deal involving star forward Phil Kessel.

Entering his draft year as one of the top European prospects, Kapanen spent most of the season with KalPa, scoring 7 goals in 47 games for a team that finished last in the league. He was expected to be an impact player for the Finland under-20 team at the 2014 World Junior Championship but was injured in the last practice before the tournament began and was unable to participate. The lost opportunity did not affect Kapanen's draft stock as he finished atop both the mid-season and final Central Scouting rankings amongst European-based skaters. With KalPa and its under-20 affiliate both eliminated from the respective playoffs, Kapanen was sent to the KalPa under-18 team for the end of their season and aided the Jr. B SM-Sarja team in its third-place league finish. Kapanen tied for the team lead in playoff goals with six despite playing in only four games. Kapanen found himself on Finland's under-18 team for a second consecutive year, but managed just two points in five games as Finland was eliminated in the quarter-final round following a heavy 10–0 loss to Sweden.

Despite being ranked as the 10th-, 13th- and 18th-best overall prospect by several NHL teams, Kapanen was ultimately selected 22nd overall by the Pittsburgh Penguins, the second-straight year Pittsburgh had selected a Finn in the first round of the NHL Entry Draft, after Olli Määttä in 2012. Jim Rutherford, the Penguins' general manager at the time, had also drafted Kasperi's father when he was general manager of the Hartford Whalers in 1995. On 11 July 2014, Kapanen signed a three-year, entry-level contract with the Penguins.

On 12 January 2013, Kapanen played alongside his father Sami Kapanen in a SM-liiga game.

Kapanen spent parts of the 2012–13 and 2013–14 seasons playing with his father for KalPa in the SM-liiga.

Prior to the 2004–05 NHL lockout, Kasperi Kapanen's father, Sami Kapanen, was part of a group that purchased the latter's junior team in Finland, KalPa. Having owned the team since, it was no surprise when Kasperi Kapanen made his bantam debut with KalPa's under-16 affiliate in the Jr. C SM-Sarja. Kasperi Kapanen led the team in goals and was second in points, though failed to help them win their playoff qualifier. The following year, as a 15-year-old, Kasperi spent only eight games on the under-16 squad (scoring 16 points in the process) before graduating to the under-18 team playing in the Jr. B SM-Sarja. Kapanen continued his torrid scoring with 24 points in 25 games, finishing second in both goals (13) and points. His third season in Finland's junior system saw more of the same as he swiftly advanced to the under-20 team playing in the Jr. A SM-Liiga and recorded 29 points in 36 games, again leading the team in goals (14) and finishing fourth in points. During the 2012–13 season, he also spent 13 games with the senior KalPa team in the SM-Liiga, Finland's top professional league, playing alongside his father. At the end of the year, Kapanen was selected to play for the Finland under-18 national team at the 2013 IIHF World U18 Championships. Kapanen led Finland in goals and was second in points as he helped the team to a bronze medal finish.

Kasperi Kapanen (born 23 July 1996) is a Finnish professional ice hockey forward for the Toronto Maple Leafs of the National Hockey League (NHL). He made his Liiga debut playing with KalPa during the 2012–13 SM-liiga season. Kapanen was selected by the Pittsburgh Penguins in the first round, 22nd overall, of the 2014 NHL Entry Draft.