Oleksandr Usyk vs. Derek Chisora, billed as Fright Night, was a professional boxing match contested between former undisputed cruiserweight champion and the WBO's heavyweight mandatory challenger, Oleksandr Usyk, and WBO Inter-Continental heavyweight champion, Derek Chisora.

Usyk became the first ever four-belt undisputed cruiserweight champion in 2018 after winning the World Boxing Super Series tournament.

[1] Following his victory over Tony Bellew later in the year, Usyk made the decision to move up to the heavyweight division in 2019.

[4] Scoring a UD victory over Senad Gashi in April, and a second round KO over former world title challenger Artur Szpilka in July, a fight in which Usyk was in attendance.

Sky Sports’ Head of Boxing Development Adam Smith, described the fight a "classic Heavyweight clash".

[10] As part of his preparation for his bouts, Usyk sparred occasionally with former unified heavyweight champion Wladimir Klitschko.

His manager David Haye was working on getting heavyweights to spar with Chisora who could closely mirror Usyk's quickness.

Haye revealed the game plan was not to outbox Usyk, but to make the fight rough and high pressure from the start.

[20][21] On 30 March, the British Boxing Board of Control extended the suspension until he end of May, following the guidelines from government and medical authorities, meaning the fight would be postponed.

In the middle rounds, Usyk was able to control the pace, using his superior movement and footwork to lead with solid jabs and land combination punches from angles on the outside, outboxing Chisora and escaping his attacks.

In the later rounds, Chisora upped his output and remained on the offensive, pressing forward and successfully landing a series of hard right hands and body shots, with Usyk responding with several heavy flurries and scoring stiff blows repeatedly.

[35] Usyk defeated Joshua on 25 September, by unanimous decision to capture the unified WBA (Super), IBF, WBO and IBO titles.