That was the case back in March, when Carter-Williams and Syracuse got the best of Oladipo and Indiana in the Sweet 16 of the NCAA tournament.
And it was evident again Thursday, as the two promising guards reunited in the final game of the day at the Orlando Pro Summer League.
This time, Oladipo struck back to hit the game-winning shot over Carter-Williams with 4.4 seconds left in Orlando's 90-89 win against Philadelphia. And if these two keep this up, it just might turn into the NBA's next big point guard rivalry.
"That's the beauty of competition," Oladipo said Thursday. "I know Mike from a while ago, and he beat me in the Sweet 16. So I wanted this one. He's a cool dude and a good friend of mine. But at the end of the day, when we get on the court, we're trying to go at each other's neck."
At the same time, Oladipo and Carter-Williams are trying to get a firm grasp on becoming productive NBA point guards with teams in the midst of major rebuilding projects.
Oladipo, the No. 2 overall pick by the Magic, had his best game of the weeklong summer league Thursday as he makes the difficult adjustment from being a college wing scorer to becoming a professional point guard. As Orlando's highest draft pick in nearly a decade, he's also replacing Dwight Howard as the face of the franchise.
Meanwhile, Carter-Williams went to Philadelphia as the No. 11 pick. He joins a team that just lost center Andrew Bynum in free agency to Cleveland without compensation and traded its lone All-Star, point guard Jrue Holiday, to New Orleans for No. 6 pick Nerlens Noel, who will miss the start of the season to recover from knee surgery.
But none of those difficult predicaments seemed to matter to either Oladipo or Carter-Williams for at least a day, as they turned a rather meaningless summer league game into something that felt so much more significant, with each answering the other with highlight plays Thursday.
Oladipo scored 24 points with six assists, three rebounds and three steals in 36 minutes. Carter-Williams had 11 points, nine assists, six rebounds and a block in 33 minutes. The 76ers' floor leader also had a specific request for summer league coach Michael Curry after spending early stages of the game guarding someone other than Oladipo.
"When I wasn't covering him throughout the game, I kept asking Coach if I could cover him," Carter-Williams said. "He's a great player. We're cool off the court, so we're good friends. To be competitive on the court is just a fun thing."
It almost seemed like this past spring all over again.
The stage then was the Verizon Center in Washington, D.C., where Carter-Williams spearheaded a dominant team defensive effort and finished with a game-high 24 points, five rebounds and four steals in Syracuse's 61-50 victory. Oladipo countered with 16 points and three steals as the top-seeded Hoosiers struggled against the zone defense and were held to their lowest scoring output of the season.
This time around, their teams exchanged the lead 17 times Thursday before Oladipo found himself isolated at the top of the key with Carter-Williams defending and the Magic trailing by a point in the final seconds. Oladipo cut to his left, then stepped back for a jumper on the wing over Carter-Williams' outstretched arms that swished through the net.
"Yeah, it felt a little bit like deja vu," Carter-Williams said, referring to their last matchup. "But [Oladipo] got the better of me this time, I think, with that last shot. But you know what? We'll have our time again, though."
Both players look forward to extending their rivalry on the next level, although they also acknowledge there are many areas in which their respective games need major development.
Carter-Williams ranks among the 10-team summer league's leaders in assists (29) and turnovers (21) through four games and is shooting just 26.1 percent from the field entering Friday's final matchups. Still, Carter-Williams has shown superior confidence and passing ability at the position compared to the two other point guards in Orlando taken in last month's lottery -- Oladipo and Trey Burke.
Oladipo and Carter-Williams combined to miss 16 shots and accounted for 13 turnovers, so there are plenty of kinks to work out as they settle into primary roles when NBA training camps open in about three months. But there also was no shortage of promising plays from both this week, culminating in the latter stages of Thursday's game.
"I think both of them had turnovers that were higher than they will be," Curry said. "It's tough coming in as a rookie point guard, trying to learn everything and then trying to make plays and do everything for your teammates. So far, both of those guys have been playing very well despite their shooting numbers and despite their turnovers."
Curry said Carter-Williams has been as engaged with the coaching staff off the court as he's been aggressive on it with his teammates during games.
"Every day, he brings it. Every practice, he asks questions," Curry said. "It's not one thing we go over he doesn't ask questions about. He asks questions at halftime. He's aware of everything, and sometimes players that have a chance to be great in this league, you can see that in him."
Oladipo also envisions rapidly developing into a great player in Orlando and settling comfortably at point guard. His game-winning shot offered a hint of his big-play potential in the league, but Oladipo also said he doesn't consider himself a true NBA player just yet.
"No. I'm not officially an NBA player until I play in a real game," he said. "And I'm looking forward to that day. I know it's going to be a rush, that first game out there. It's basketball on an elite level."
For many of the top prospects, this week has been about providing an initial confidence boost and a running start. That's especially the case for Oladipo and Carter-Williams, who are entering the league at easily the deepest and most talented position.
"We can compete against the guys that are already there," Carter-Williams said. "I know [Oladipo is] going to keep working, and so am I. Right now, we're kind of at the bottom of the pedestal. We're chasing guys like Chris Paul and Russell Westbrook. We're trying to get at their level."
Both prospects have plenty to look forward to as rookies.
On Thursday, they simply enjoyed reaching back and providing another thrilling battle against one another. Fans aren't generally permitted into the Magic's practice facility for summer league. But a few season-ticket holders and guests of team executives gathered in the suite level overlooking the practice court where games are held.
Among that group were a few who wore Hoosiers team apparel, including Indiana's red-and-white striped pants. They started cheering after every play Oladipo made.
"You dream about moments like that all the time, whether it's in the summer league or in front of your house, and you go, '3, 2, 1,'" Oladipo said, reliving the moment leading up to his game-winning jumper. "It's stuff like that you live for. Being able to make a big shot builds my confidence."
Once the shot went in, fans chanted, "O-la-di-po," in unison.
It didn't quite erase the taste of Indiana's loss to Carter-Williams and Syracuse in the NCAA tournament.
But for Oladipo, it came close enough.
"It means a lot to me, because I thought I'd never hear those chants again -- not for a while, at least," Oladipo said. "It just shows you how much love you get once you wear those candy-striped pants. You'll always be a Hoosier, and they'll come out to watch you no matter where you are."
In this faceoff, Oladipo might have evened the score.
Carter-Williams vows there will be many more.