Unfortunately, Holloway would suffer a wrist injury in the NCAA playoffs, undergoing surgery to repair a scaphoid bone fracture in March of 2021. His wrist did not heal enough in subsequent months, and he was forced to undergo a second surgery in September of 2021, causing him to miss the start of the 2021-22 season.

In January of 2022, Holloway was finally cleared to play with Edmonton’s AHL affiliate, the Bakersfield Condors, producing a total of 22 points in 33 games with Bakersfield. This production was nothing exceptional, but of course, recently coming off two wrist surgeries undoubtedly had an impact on his performance. It’s also worth noting that his on-ice expected goal differential ranked first among Bakersfield’s forwards, so there was likely some bad puck luck at play as well. Holloway would then produce four points in five AHL playoff games, but the Condors were eliminated in the second round by the Stockton Heat.

Still, that was not the end of Holloway’s 2021-22 season. The Oilers reached the Western Conference Finals that year, playing the eventual cup-winning Colorado Avalanche. With Evander Kane suspended after a hit on Nazem Kadri in Game 3 of the WCF, Edmonton inserted Dylan Holloway into their lineup in Game 4. Although he played just three minutes, and the Avalanche ultimately swept the Oilers, it was Holloway’s NHL debut.

In 2022-23, a healthy Holloway had an opportunity to play considerable minutes in the pre-season, and ended up impressing the Oilers coaches, with 6 points in 5 games and a 66 percent goal differential at 5v5. Then-head coach Jay Woodcroft would deploy Holloway on the second line next to Leon Draisaitl and Warren Foegele on opening night against the Vancouver Canucks, in Holloway’s regular-season NHL debut; however, he played just 58 seconds next to Draisaitl in that game.

On his very first regular-season shift in the NHL, he made a turnover to Elias Pettersson, resulting in an early 1-0 lead for Vancouver. Fortunately, Edmonton would go on to win that game, but Holloway played a mere eight minutes. Ever since, Woodcroft rarely deployed Holloway in a meaningful role, as he averaged nine and a half minutes in 51 games with Edmonton. He amassed just nine points, although he did possess decent underlying numbers with a 53 percent expected goal differential.

As a result of Edmonton’s cap situation, they sent Holloway down to Bakersfield a few weeks before the trade deadline, but unluckily for him, he would immediately be injured in his first AHL game, missing roughly a month of action. Holloway would end the 2022-23 season with 12 AHL regular-season games and 2 AHL playoff games.

In 2023-24, the Oilers began the year in an extremely tight cap situation once again; with Holloway on his ELC, he was a lock to begin the year on the NHL roster.

However, Edmonton had the worst start to a season in franchise history, with a 3-9-1 record in their first 13 games of 2023-24. Although Holloway did post strong possession numbers, with an expected goal differential of 62 percent, his actual goal differential was an abysmal 32 percent, and he produced just a single point in those thirteen games. Edmonton would go on to fire head coach Jay Woodcroft, and hire Kris Knoblauch in his place.

But, on November 13 in a game against the New York Islanders, the very first game Knoblauch coached for Edmonton, Holloway would suffer yet another injury, this time to his knee. He would be subsequently placed on long-term injured reserve.

From there, Holloway’s season would be a roller-coaster. Holloway would be activated off LTIR and sent down to Bakersfield on January 4th, playing four AHL games, and then recalled to the NHL on January 20. He would then be sent back down on January 28th to play in the AHL during the NHL All-Star Break and recalled on February 4th. To make a cap-compliant roster before the playoffs, he was demoted again to the minors on March 6, until Edmonton finally recalled him before the playoffs on April 9.

The 2024 playoffs are where Holloway had a consistent spot in Edmonton’s line-up and showed potential.

Although Holloway’s raw box score totals of 5 goals and 7 points in 25 games are nothing spectacular, he did rank 3rd on the team in 5v5 goals per hour, alongside a superb 58 percent goal differential. His most memorable moment in the playoffs came in Game 4 of the Stanley Cup Finals, where he produced just his second three-point game of his NHL career, producing two goals and an assist.

Holloway spent significant time on Leon Draisaitl’s wing, playing 131 TOI (45% of his TOI) on the second line in this run. The two showed significant chemistry together, as the Oilers held a 59 percent goal differential and a 54 percent expected goal differential with Holloway and Draisaitl on-ice at 5v5.

What could he bring to the Oilers in 2024-25?

Throughout his NCAA, AHL, and NHL career, Holloway has proven a couple of things.

Firstly, he is excellent in transition. Per Mitchell Brown’s tracking data, Holloway was consistently one of the NCAA’s top transitional players, ranking ahead of several prominent players in transition efficiency score in his draft year such as Trevor Zegras and Cole Caufield. His potential has continued to show in the NHL; per our microstat tracking project, Holloway ranks 5th on the Oilers in 5v5 zone entries per hour throughout the past two seasons. It is evident that he is quite good at moving the puck up the ice effectively and efficiently using his skill and speed.

Furthermore, Holloway has consistently been a strong possession player. Teams always manage to out-play and out-chance the opposition with Holloway on-ice, primarily as a result of his transitional and forechecking abilities. He holds a career xGF% of 55 percent in his career.

On the other hand, Holloway has yet to be a major offensive threat at the NHL level, and he was not a brilliant producer in the AHL. Moving forward, he has to improve at generating more offence off his zone entries. His production has likely been heavily influenced by his injury-history, which is also a concern; he has missed significant time due to some sort of injury in each of his past three seasons, which has very likely affected his development.

That being said, Edmonton’s development of Holloway as a prospect has been far from preferable. Due to their tight cap situation, largely as a result of cap mismanagement, Holloway has constantly had to rotate between the NHL and the AHL, often preventing him from having a consistent spot in the lineup. Furthermore, I would also argue he has been improperly deployed at times, as he was often immediately benched after making a mistake, particularly by Jay Woodcroft. It’s reasonable to say he never had an extended opportunity with good players until the 2024 playoffs.

Heading into 2024-25, it is likely that Holloway begins the season in the bottom-six, perhaps next to Adam Henrique on the third line. This is a duo that could stylistically pair well; Henrique is one of Edmonton’s significantly older and slower players, with very subpar zone entry rates, which is an area where Holloway could be incredibly beneficial. Holloway could be the third-line’s primary puck-transporter, while he would also benefit himself from Henrique’s experience and strong middle-six production rate.

However, I’d wonder if Edmonton’s most optimal second line is a trio of Holloway, Leon Draisaitl, and Viktor Arvidsson.

These are three players that all excel at moving the puck. If Holloway progresses, this is a line that would be exceptional and dangerous off the rush. This option additionally allows for one of Jeff Skinner or Ryan Nugent-Hopkins to be on the third line, balancing and spreading the wealth throughout the line-up.

Looking ahead, 35-40 points could be a reasonable projection for Holloway. Draisaitl’s most common linemate in 2023-24, Warren Foegele, managed to produce a total of 41 points, 37 at 5v5 (one less than Aleksander Barkov!). If Holloway rotates between the second and third line, it would be a very achievable target for him. If he gets a lengthy look in the top-six, and if Edmonton decides to run a second PP unit in 2024-25 with Holloway on it, perhaps there’s even an outside chance of coming close to 50 points. But, of course, it all depends on how Edmonton deploys Holloway, and especially if he can finally remain healthy.

It will be interesting to observe how the Oilers deploy their incredibly deep forward core throughout the upcoming season and what it will all mean for Holloway.