Glover stay: 2 transfer regrets Middlesbrough should have following summer window | OneFootball

FLW takes a look at two pieces of business that Middlesbrough may regret not completing from the summer transfer window.

Middlesbrough's summer transfer window was largely a very successful one, with key players retained and strong additions to Michael Carrick's squad being made.

Aidan Morris, Tommy Conway, and Delano Burgzorg are among Middlesbrough's summer signings that have already made an impact on Teesside, whilst new recruits such as Neto Borges, Ben Doak and Micah Hamilton will be looking to play big roles for Boro as the season progresses.

But just as important as it is to make strong additions to your squad, it's equally as vital that you're able to keep hold of prized assets, especially if the club harbours promotion aspirations, as Middlesbrough do this year.

As such, fending off interest in their star players such as Emmanuel Latte Lath and Rav van den Berg sent a clear message of ambition from the club's hierarchy, with Carrick now appearing to have all the tools to put together a memorable season in the North East.

But, are there some pieces of business that weren't finalised that Boro could regret in the future? Football League World investigates...

Boro missed an opportunity to cash in on Tom Glover

Seny Dieng was always going to reprise his role as Middlesbrough's number one goalkeeper this season, after an impressive enough debut season at the Riverside last term.

The real intrigue at the goalkeeper position this summer was centered around who would be backing him up, with Boro possessing a stable of talented young goalkeepers itching for first team action.

One of those was Sol Brynn, who returned to Teesside after enjoying his latest successful loan spell away from the club, this time with Leyton Orient, where he made 42 appearances and kept 13 clean sheets in League One last season.

The first real evidence Boro fans were going to get on who'd won that battle would come in the club's Carabao Cup first round tie away at Leeds United, and it was Brynn who got the nod.

A 3-0 win, a clean sheet and an assured performance from the 23-year-old has seen him make the Middlesbrough bench in every Championship game since, with Glover being absent from matchday squads in the league since the opening day.

With no first team appearances so far this season, and no doubt having concerns over his domestic and international future because of this, the 26-year-old will likely not be content as the number three keeper.

Reports from Australia earlier in the summer had revealed that Glasgow giants Celtic and Rangers were both interested in the Aussie, whilst Danish side Copenhagen were also keen on a move for the former Melbourne City shot-stopper.

Had Middlesbrough decided to cash in, they could well have received a respectable fee for Glover. But after opting to retain his services until January at least, Glover's value will only serve to fall the longer he goes without the opportunity to raise it via first team minutes.

Matthew Hoppe will be losing any remaining value

Since arriving from RCD Mallorca in a deal worth a reported fee of £2.5m, it's perhaps an understatement to say that Matthew Hoppe's Middlesbrough career has not gone to plan.

Whether it was the emergence of Championship golden boot winner Chuba Akpom, the presence of other quality strikers such as Cameron Archer, or the signing and resulting form of Latte Lath, everything that could've gone wrong for the American international, pretty much has.

The 23-year-old hasn't made a first team appearance for Middlesbrough since Boxing Day 2022, and after not being handed a squad number for the 2024/25 season, Hoppe now appears firmly doomed to academy football at best in the North East this term.

Middlesbrough were understood to be trying to sell Hoppe this summer, with a move back to the MLS seeming like a foregone conclusion. But, Boro chiefs couldn't find a dance partner, and thus, the forward saw the exit door slammed in his face.

Resigned to the shadows this season, like Glover, Hoppe's value will only continue to fall the longer he remains out of the picture, and with no route to first team football in sight, the club may well have missed their chance to get a fee back for the striker by not selling this summer.

Contracted with Middlesbrough until the summer of 2026, any interested parties between now and then may well observe his situation at Boro and wait until he hits the free agent market, rather than pay a fee for him.

It's a real shame to see, as Hoppe arrived at the Riverside with a Bundesliga hat-trick to his name, and was a player who was hoped could have the potential to lead the line for the club for many years to come.