When the Toronto Raptors made the Kawhi Leonard trade, everything changed. This team went from an up-and-coming playoff team to a group with a championship-or-bust label. While I was sifting through Toronto’s schedule for the 2026-27 season, a four-game sample at the end of November and into the start of December caught my eye. This sample of games features the Denver Nuggets (Nov. 29), Houston Rockets (Dec. 1), Oklahoma City Thunder (Dec. 3) and San Antonio Spurs (Dec. 13).
The reason this specific sample of games caught my attention isn’t just because they are good teams, but because they are all serious threats to make it out of the Western Conference next season. For the Raptors, if they were to make it out of the Eastern Conference, they’d likely be meeting one of these four teams in the Finals, making this winter sample of games very telling.
Jokic isn’t going to be the problem
Say what you want about the Denver Nuggets, but any team that is led by Nikola Jokic in the prime of his career is going to be a contender in my eyes. From a matchup standpoint on paper, the Raptors may have the tools to neutralize the ‘Joker’. Between Collin Murray-Boyles, Kawhi Leonard, Scottie Barnes, and Jakob Poeltl, Toronto has more than enough different bodies they can throw at the four-time MVP. But that might be where the Raptors' issues start.
​Because with Jokic demanding so much attention, it raises concerns about who is picking up Canada’s own Jamal Murray. The 29-year-old is coming off a career-best season in which he made an All-Star appearance and an All-NBA team, and the Raptors' lack of defense from the guard spot could be problematic. Toronto’s chances in this game and in a potential series with Denver could depend heavily on how their guard room defends Murray.
Houston will test Toronto physically
Now to the Houston Rockets, who probably received some scoffs when I mentioned them as contenders, even though they have all the makings of a contender. Sure, last season didn’t go as planned, but they spent all of 2025-26 without a true organizer because Fred VanVleet was watching from the sidelines. With the former Raptors All-Star guard back in the mix, Houston has a very complete starting five and a bench full of young guys who are only bound to get better.
Oh, and they have that Kevin Durant dude, you know the greatest scorer ever.​
Out of the four teams in this sample, the Rockets may be the best matchup for the Raptors, mainly due to Leonard matching up so well with KD. However, how Toronto fights against Houston’s physical, offensive-rebound-heavy style of play could give fans a better sense of how they'd hang with the Rockets in a potential Finals matchup.
OKC is the ultimate test
Next on the schedule is the 2025 NBA champions and Western Conference runners-up from last season, the Shai Gilgeous-Alexander-led OKC Thunder.
This is where things get real.
While I would still classify the Rockets and Nuggets as contenders, OKC may be in a tier of its own among teams coming out of the West. Their depth, defense, coaching and star power might truly be unmatched around the league.
They have a big three between SGA, Jalen Williams and Chet Holmgren that could pose a ton of issues for the Raptors. In this type of matchup, CMB would be crucial as Darko Rajakovic would likely assign Leonard to SGA, and Barnes to J-Dub, leaving Holmgren as the matchup that needs to be solved. We’ve seen in the past that Holmgren struggles with physicality and stronger defenders, making it an obvious key to put CMB on him for an entire game or series if these two teams were to meet in the Finals.
If I were putting money on who's making it out of the West this season, it would be OKC, which is why the results from this early matchup could be so important to Toronto’s 2027 title odds.
Wembanyama will present an out-of-world challenge
Last is the Spurs. Now, San Antonio isn’t just a contender because they were in the Finals last season, but because they will be another year into the careers of Victor Wembanyama, Dylan Harper, Stephon Castle and Carter Bryant. On top of that, they retained their other core players and added Tobias Harris to slot in at the four and be another floor spacer.
The Spurs are the real deal, and playing them on the road with Leonard back in San Antonio is going to be a tough atmosphere for the Raptors. Unlike other teams' stars, there’s no real answer for Wemby other than having your best perimeter defender front him and a big in the back providing help. Even then, there’s no guarantee you’re going to stop him. Seeing the way the Raptors scheme defensively and attack, the Spurs will be a nice test and give fans a look into what this team could be capable of if they make it to the NBA Finals.
Four games against four real contenders from the Western Conference that all present different challenges. For a Raptors team with title aspirations, there’s no bigger test than this sample.
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