Kanchelskis began his career with his hometown team Zirka Kirovohrad in 1986, before transferring to Dynamo Kyiv in the Soviet Top League, and later to rivals Shakhtar Donetsk.

[4] Lobanovskyi favoured a 4–4–2 formation, a system which focussed on getting the ball to the flanks and crossing into the penalty box,[3] which Kanchelskis describes as an "English style of play".

[5] Kanchelskis eventually decided to leave Dynamo due to lack of game time, causing upset to his mentor Lobanovskyi, who he admired and respected greatly.

[9] Ferguson had discovered Kanchelskis through a VHS tape sent to him by Norwegian agent Rune Hauge,[10] and had been able to personally scout him during a Soviet Union match against Scotland.

However, compensation for Kanchelskis and his teammates had come at Wembley Stadium on 12 April 1992 when a 1–0 win over Nottingham Forest gave them their first ever Football League Cup triumph.

Kanchelskis was sent off in the last minute of the League Cup final for deliberate handball; Dean Saunders scored from the resulting penalty, ensuring a 3–1 loss to Aston Villa,[17] a defeat which eventually cost United a domestic treble.

United were also without the suspended Eric Cantona (who was banned for eight months after he assaulted a spectator against Crystal Palace in late January), while Andy Cole was cup-tied for the FA Cup games.

Bryan Robson made an approach to sign Kanchelskis for Middlesbrough when it was announced that United would be selling him, bidding £4.5m in July 1995, while there was also interest from Arsenal.

[20] Kanchelskis confirmed that he would be leaving United, blaming Ferguson for his imminent departure,[21] and eventually agreed to join Everton in August, but the transfer was cancelled due to a claim by Shakhtar Donetsk for money.

[25] United manager Ferguson later claimed in his autobiography that he was offered a bung of £40,000 to force through a transfer by Grigory Essaoulenko,[26] the agent of Kanchelskis, who denied the allegations.

[38] A week later, he put in a Man of the Match performance in a 2–2 draw with Sheffield Wednesday, scoring Everton's first three minutes into injury time in the first half, before assisting the equaliser for Daniel Amokachi.

[40] On 24 February 1996, Kanchelskis scored the opening goal in a 3–0 win against Nottingham Forest, which moved them into 7th place for the first time since August, increasing their chances of UEFA Cup qualification.

[53] He changed his shirt number to 17 for the 1997–98 season, and his form improved in the opening two matchdays of the Serie A campaign, including scoring his first goal against Bari.

[59] Returning to action after 40 days in a 1998 FIFA World Cup qualifier against Italy in Moscow, he collided with Gianluca Pagliuca and suffered a fracture in his knee,[60] being sidelined until the end of January in a Coppa Italia match.

[63] After struggling to make an impact in Italy, he was allowed to leave, and signed for Scottish Premier League team Rangers for a national record of £5.5 million,[64] part of the club's total summer spending by manager Dick Advocaat of £25m.

[69] In his second season with the club, he was dropped from the team, but regained his place in the new year and eventually won the 2000 Scottish Cup Final, amidst reports he could be sold.

[76] He chose to return to Manchester,[77] and made his debut on 31 January, coming on as a half-time substitute for Andy Morrison in a 1–1 draw with Liverpool in the league.

[80] Upon his return to Rangers, he said he was happy to be back and vowed to give his all for the team,[81] but having received little game time and falling behind Russell Latapy in the pecking order, began to consider his future.

[82] After his release from Rangers upon the expiration of his contract,[83] he went on trial with Southampton;[84] manager Gordon Strachan said that Kanchelskis had personally phoned him to ask for permission to train with the club.

[105] His stay at Dynamo was short-lived when he was sacked for a "disciplinary offence" on the eve of the 2004 season, with manager Jaroslav Hřebík citing a "lack of professionalism".

[122] Kanchelskis was part of the Soviet Union U21 team which won the 1990 UEFA European Under-21 Championship, scoring a goal in the second leg of the final against Yugoslavia U21.

[128] Having struggled in the qualification for the 1994 FIFA World Cup, Russia lost to Greece, and following the match, though he had not played in Athens, Kanchelskis was one of fourteen players to sign a letter sent to Shamil Tarpishchev, calling for the dismissal of manager Pavel Sadyrin and the appointment of Anatoliy Byshovets as the replacement.

[131][132] Kanchelskis usually played as a right-winger throughout his career, where he was known for his work-rate, pace, explosive acceleration, powerful shot from range, and eye for goal; however, he was not particularly strong in the air.

[133] Under his manager Lobanovsky at Dynamo Kyiv, Kanchelskis operated as a traditional "English style" winger in a 4–4–2 formation, looking to receive the ball out wide and cross into the box from the touch-line.

[4][3][5] Shortly after his retirement as a player in February 2007, Kanchelskis became the sporting director of First Division team FC Nosta Novotroitsk,[134] with the intended goal of improving the infrastructure of the club.

[144] Competing in the Second Division, the club began their first league season on 24 April, with Kanchelskis guiding his team to their first ever win, a 3–1 victory against Tyumen, with striker Konstantin Ionov scoring all three goals.

[151] He was the replacement for Bulgarian manager Gosho Petkov, who had gained 8 points from 28 games, and had left them in last place in the league table,[152] but Kanchelskis failed to avoid relegation.

[157] On 9 October 2018, Kanchelskis was appointed manager of the Uzbekistan Super League team Navbahor Namangan, replacing Ilkhom Muminjonov in the role.

[161] In June 2019, Kanchelskis resigned from his role, citing the unsatisfactory results which had left the team situated in 4th place in the league, having earned 18 points from 12 games.

[168] In October 2020, with the team in 7th place in the league after 18 matches,[169] Kanchelskis left Navbahor for a second time, on this occasion due to being unpaid for four months,[170] and submitted an application to FIFA.