Huddersfield Town can land Leo Castledine 2.0 with £1m Aston Villa transfer raid | OneFootball

Tommi O'Reilly has shone in League Two this season and could follow in Leo Castledine's footsteps at Huddersfield next year

Huddersfield Town were left to rue another disappointing campaign this season, as they failed to finish inside the play-offs for the second straight year.

A lot of questions will be asked in the summer as to where things went wrong for the Terriers this season, as they look to finally achieve the lofty expectations they set themselves and secure promotion back into the Championship.

From the points dropped from winning positions right at the end of the season, to allowing Joe Taylor to leave the club on loan in January, there's a lot of 'what ifs' that have surrounded Huddersfield and whether, if things were different, they would have at least finished in the top six.

But arguably the most important 'what if' of them all is what would have happened if Leo Castledine had remained at Huddersfield throughout the entire campaign.

The 20-year-old Chelsea loanee set League One alight in the final few months of his time at the Accu Stadium, scoring eight goals and assisting one in the 10 games preceding the Premier League side's decision to terminate his loan and sell him to Middlesbrough.

Tommi O'Reilly could be Huddersfield Town's Leo Castledine replacement

Castledine's 10 goals this season ended up topping Huddersfield's goalscoring charts for the entire season in League One.

The Terriers weren't able to replace his quality in the final third in January, so one of the primary focuses this coming summer will be to bring in someone young, exciting and dynamic, who can play either through the middle or out wide, and Tommi O'Reilly needs to be at the top of their list.

Huddersfield have been credited with interest in the Aston Villa wideman, who spent the 2025/26 campaign on loan in League Two with Crewe Alexandra. The Premier League side is reportedly open to selling the 22-year-old for £1 million.

O'Reilly, like Castledine, had a bit of an underwhelming loan spell at Shrewsbury Town in the 2024/25 campaign. So underwhelming, in fact, that while Castledine was kept on at Croud Meadow, the 22-year-old was sent back and relocated to MK Dons in League Two. Even then, he struggled to make an impact.

Aston Villa would once again loan him out to League Two this season, and at Crewe, he's been electric.

O'Reilly started every game in the fourth tier for the Alex, scoring seven and assisting a league-high 11, while creating the third-most big chances in the entire division, according to Fotmob.

Evidently, the 22-year-old has proven that he is better than League Two level, and, understandably, Huddersfield are going to have to battle lower-end Championship side Portsmouth and fellow top-end third-tier outfit Oxford United for his services.

Huddersfield Town need to make sure they beat Oxford United and Portsmouth for Tommi O'Reilly transfer

While O'Reilly has clear potential to make it in the Championship and beyond, the step-up to the second-tier may be a step too far for the 22-year-old right now, meaning that a top-end League One side would be a more likely destination.

If that proves to be the case, Huddersfield will need to outmuscle an Oxford side who have spent the last two years in the Championship and will be targeting an immediate return to secure his services.

Despite the Yellows' recently relegated status, though, the Terriers' position as one of the more highly-backed sides in the third tier will put them on par with Matt Bloomfield's side, and you'd imagine that, if Huddersfield really want to pursue O'Reilly, there may be little stopping them from getting what they want.

Promotion out of League One this time next year is almost the only option for Huddersfield. Kevin Nagle's impassioned tweet last month stated that the higher-ups at the Accu Stadium will be "working day and night to get it right" during the summer and that "we will get there, or we will die trying."

And while that doesn't indicate throwing money at everyone just to see who sticks, it does infer that they'll be looking to put Liam Manning, when he returns, in the best possible position to get promoted.

O'Reilly is a Championship player in the making, but perhaps needs one year in League One to fully cement that. Huddersfield needs to make sure that they're the side to facilitate that year.