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NBA Cup rivalry? Raptors and Knicks have a history that includes lawsuits and big trades

The Athletic has live coverage of the 2025 NBA Cup quarterfinals.

With players changing teams faster than ever before, the concept of sustained rivalries between NBA teams appears to be fading away. Perhaps the Golden State Warriors and Memphis Grizzlies came close a few years back as animosity built between the two teams, but that’s fizzled out as Ja Morant’s career has been rocked by unavailability.

So no, the Toronto Raptors and New York Knicks are not rivals. Neither team’s fans sit around thinking about how much they hate one another, nor do the players.

Yet the two teams, which play in Tuesday’s NBA Cup quarterfinals, do have a fair amount of shared history, especially considering this is just the Raptors’ 31st season.

• The Knicks beat the Toronto Huskies at Maple Leaf Gardens in the first-ever NBA game on Nov. 1, 1946. Leo Gottlieb paced the Knicks with 14 points, while Ed Sadowski had 18 for the Huskies, who disbanded after a 22-38 season.

ON THIS DAY (Nov. 1, 1946) the FIRST NBA game took place in TORONTO as the New York Knicks took on the Toronto Huskies in front of 7,090 fans! 🇨🇦

Fans that were taller than the tallest Huskies player (6’8”) got in for free. pic.twitter.com/sCZh6RmH6C

— NBA Canada (@NBACanada) November 1, 2024

• The two teams played each other in the first round of the playoffs in back-to-back seasons in 2000 and 2001. It was the first time the Knicks swept the Raptors in the postseason. During the series, Raptors coach Butch Carter sued Knicks center (and former Raptors draft pick) Marcus Camby for defamation and then quickly dropped the suit. Camby, traded to New York for Charles Oakley before the 1999 season, had called Carter a liar and said his team’s players didn’t like him. Carter was fired that offseason.

The Raptors won the second time, essentially ending the Knicks’ run of success. After that series, New York won just one playoff series over the next 21 seasons.

• After getting the best of the Knicks in the Carmelo Anthony trade when he was the general manager in Denver, Masai Ujiri, in one of his first moves in charge of the Raptors, traded Andrea Bargnani to the Knicks. In one of Ujiri’s first moves in charge of the Raptors, Toronto received a package that included the first-round pick that became Jakob Poeltl. That was another clear win for Ujiri, which reportedly made the Knicks hesitant to make another trade with the executive.

The Raptors were close to trading Kyle Lowry to New York shortly after trading Rudy Gay to Sacramento in December 2013. That trade fell through. We’ll never know how much Knicks owner James Dolan’s reticence to deal with Ujiri again had to do with the last-minute change. However, Lowry became a six-time All-Star as part of a seven-year playoff streak for the Raptors that included six division titles and a championship.

In those same years, the Knicks failed to make the playoffs even once.

• The Knicks sued the Raptors in 2023, alleging that video coordinator/assistant coach Ike Azotam, whom the Raptors hired away from New York as new coach Darko Rajaković built out his staff, sent confidential files to the Raptors while he still worked for the Knicks. The Knicks sued for $10 million in damages, and the pair of teams submitted court filings painting the other as petty and/or incompetent.

Dolan’s relationship with Raptors part-owner Larry Tanenbaum was fraught, partly because Tanenbaum is the chairman of the NBA’s board of governors. Dolan has disagreed with commissioner Adam Silver repeatedly over the years and has reportedly often cast the lone dissenting vote in board of governors decisions.

The two teams agreed voluntarily to dismiss the lawsuit in October. Notably, the lawsuit went away only after Rogers Communications took over majority ownership of Maple Leaf Sports and Entertainment, the company that controls the Raptors, among other sports and entertainment properties, lessening Tannenbaum’s power. The teams still managed to complete a December 2023 trade that sent OG Anunoby to New York and RJ Barrett and Immanuel Quickley to Toronto.

All of which essentially makes Tuesday night’s game the “Petty Bowl” of the 2025 NBA Cup.

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