The Raptors are set to play the New York Knicks in the first elimination game of the Emirates NBA Cup on Tuesday, another milestone in a season that has exceeded expectations so far for Toronto.

Toronto swept their Group A competition in the round robin and were the first team in the National Basketball Association to clinch a spot in the knockout stage.

Raptors general manager Bobby Webster is excited about the strong start to the year, but recognizes that the hard work is still to come – starting on Tuesday.

Webster joined First Up on TSN1050 on Tuesday morning to discuss the Emirates NBA Cup, the start to the season and what he’s liked about the team to this point.

“Considering we’ve had a little bit of a rough stretch, it should be fun, exciting, to get back into Cup mode,” Webster said on Tuesday.

The Raptors enter this game against the Knicks at 15-10, but have lost five of their last six, including a 116-94 blowout loss against the Knicks on Nov. 30.

It has been a sharp downturn from the nine-game winning streak that preceded this rough stretch, which included the four victories in the NBA Cup in which they beat their opponents by an average of 13.8 points per game.

“The players, there’s a little bit of chatter in the locker room [as] we won a couple of games and they’re really competitive, so what if we win the next game? What’s the point differential? It’s like a mid-season, European soccer-cup type tournament, you gotta win games and win by a lot, qualify for the knockout round, so it’s been fun,” Webster said.

This is the third iteration of the NBA Cup, and the Raptors won a combined two games in the first two years of the competition.

“It’s been fun to be a part of it. We haven’t really had meaningful Cup games so far, so here we are in year three. If we win this game we get to go to Vegas so there’s a lot of fun things surrounding it. But at the end of the day it’s sort of win or go home, playoff, March Madness-type atmosphere. That’s the appeal of it and we’ve been fortunate enough to have been a part of it this season,” Webster said.

More than just winning games for the eventual playoff chase, Webster values how playing competitive games in the NBA Cup can help build a mentality for meaningful basketball late in the season. The Raptors haven’t advanced beyond the play-in tournament since the 2021-22 campaign.

“[The NBA Cup is] designed for these up-and-coming teams. We talked about it at the league level, four or five years ago. People said, ‘Why are the players going to care?’” Webster said. “I think we saw the Indiana Pacers before their [Finals] run last year, they were competitive in the Cup, Oklahoma City’s been competitive in the Cup. I do think it’s a little bit of a precursor to if you want to become a competitive team, if you want to be a contender, [it helps to] play well here, get some reps under your belt before the real games start in April and May.”

Tuesday’s game against the Knicks will be one of the biggest of the season for the Raptors. It’s a chance to topple an elite Eastern Conference rival, a chance to show that the team can fight through their recent struggles and a chance to show that the early success can translate when it comes to more competitive contests in the new year.

“It’s been a really positive start,” Webster said. “I think the camaraderie which we tried to build on, the culture that Darko [Rajakovic] instilled when we brought him in as head coach has started to pay dividends now.

“Have we done anything? Have we won any meaningful games? No. I think the old phrase is ‘we still have to finish our breakfast,’ but it’s been a fun ride,” Webster added. “We’re 25 games in, we’ve had some really good streaks, we’ve had some tough streaks, but that’s the NBA, that’s the season, that’s what builds your character on this team.”

The Raptors’ recent struggles have coincided with the absence of guard RJ Barrett, who has missed the past eight games with a right knee sprain. With Barrett in the lineup, the Raptors are 12-5, but have gone just 3-5 with him on the shelf. The team announced on Monday that Barrett received a PRP injection and will be re-evaluated in a week.

“We’re optimistic on the prognosis based on the MRI, so thumbs up there,” Webster said regarding Barrett’s recovery. “He [scores] 20 points a night, he scores in a variety of ways – attacking the rim, catch and shoot, putting pressure on the defence in transition – so that’s [been] hard to replace.

“At times, we’ve seen our young guys step up, but they’re young still so the consistency has been a bit of a challenge for them. Other guys have had to step up so now we sort of see roles change. There’s been some bright spots there but we just need it every night. It’s a testament to how much work RJ puts in and how much he contributes so hopefully we get him back soon here and get back to our offensive production.”

Webster, who told TSN earlier in the year that it’s a good time to “pick your new favourite Raptor” because of all the new faces on the team, has continued to be impressed by the contributions of second-year point guard Jamal Shead and free agent acquisition Sandro Mamukelashvili.

“The two fun guys are Shead and Sandro off the bench,” Webster said. “They bring excitement; Jamal’s sort of attacking, dog mentality on both ends of the court and Mamu’s got a skill set that we’ve been searching for for a while: he can pick and pop, shoot the three, [and] he can attack the rim.”

Mamukelashvili leads all Raptors bench players in scoring at 10.0 points per game, and Shead leads all bench players with 5.1 assists per game. The pair are averaging just over 19 minutes a game.

“Sometimes I’m sitting there in my seat watching the game and I can’t wait until the bench comes in, I can’t wait until Jamal comes in or Sandro, so I think those [are] the two that get us excited.”

With the Raptors set to play perhaps the most meaningful game of the past two seasons on Tuesday, and with a batch of new faces on the team making encouraging contributions on a nightly basis, Webster did not try to hide his excitement.

“I always tell fans now that this is a good time to pick your new favourite Raptor,” Webster said. “A lot of the old, familiar faces are out and there’s a lot of new, young, exciting players. It’s a good time to be a Raptors fan.”