Middlesbrough: £1m signing was meant to be Darren Randolph replacement, but instead became Riverside flop | OneFootball

Dejan Stojanovic was signed as Middlesbrough's obvious replacement for Randolph, but he would endure a dismal two-and-a-half-year stay on Teesside.

Jonathan Woodgate paid £1m to bring Austrian goalkeeper Dejan Stojanovic to Middlesbrough in January 2020, in the hope he would become Boro's replacement for Darren Randolph.

Stojanovic was signed just one day after the Irish shot stopper departed the Riverside, joining Premier League side West Ham United in a deal worth a reported £4m.

With Middlesbrough's starting gloves now firmly up for grabs, the Austrian keeper appeared to be the obvious choice, and with an eight-figure fee parted with to bring him to Teesside, expectations were high.

However, Stojanovic would endure a fairly forgettable two-and-a-half years in the North East, and left a legacy as one of the club's more head-scratching signings in recent times.

Stojanovic fails to take starting spot from Aynsley Pears

Randolph had reportedly been suffering from a quad muscle injury since early November 2019, which handed the opportunity for Middlesbrough academy graduate Aynsley Pears to have a crack at the starting job.

His only previous senior experience had came via loan spells with respective non-league sides Gateshead and Darlington, but Woodgate evidently felt that the young goalkeeper was ready to make the leap to the Championship.

Pears would go on to make 25 appearances for Boro during the 2019/20 season, with his performances restricting Stojanovic to just eight in his first couple of months as a Middlesbrough player.

However, in the summer of 2020, Woodgate was sacked as Middlesbrough manager, and was replaced by Neil Warnock. Could this managerial change hand Stojanovic a fresh start at the Riverside?

The answer to that question came fairly swiftly, and that was no. Warnock signed Fulham goalkeeper Marcus Bettinelli on a season-long loan in the September of that year, and he would quickly establish himself as Boro's new number one.

This meant that Pears had been pushed back down to the number two option, which after proving himself as being ready to start in the Championship, wasn't a role he was prepared to play. As such, he made a permanent exit from the club in October, joining Blackburn Rovers.

All of a sudden, Stojanovic had been pushed up the depth chart, but unfortunately, Bettinelli was not for budging in-between the sticks, and come January 2021, the Austrian had recorded just a single appearance for Boro that season in the EFL Cup.

Therefore, he and the club made the decision that a loan move away from the club would be in his best interests at that time, and so he joined then German second division side St. Pauli on a temporary deal until the end of the 20/21 season.

Stojanovic would return to the North East in the summer of 2021, and with Bettinelli and Jordan Archer both returning to their parent clubs, it appeared that now would be his best chance at taking the starting spot for himself at the Riverside.

After all, he looked to have a fairly clear path to the number one role, or he did until Warnock made a flurry of goalkeeping additions. Joe Lumley arrived from QPR on a free transfer, and experienced shot stopper Luke Daniels also signed on a free from Brentford.

In the blink of an eye, Stojanovic had seen his best chance at becoming Middlesbrough's number one since joining the club disappear, and it was Lumley who won the starting gloves for Warnock.

Despite a mistake-laden campaign, he was able to largely retain his spot in the Boro starting XI, and when it was time for Warnock to rotate, it was Daniels that was given the nod over Stojanovic.

So, when the January window of 2022 came around, Boro's Austrian once again found himself leaving on loan after failing to make a single appearance that season. The German second tier was his destination again, this time joining Ingolstadt until the end of the season.

After having not played for Boro since September 2020, Stojanovic called time on his fairly disastrous Middlesbrough career in the summer of 2022, as he joined German second division outfit SSV Jahn Regensburg.

He did so with one-year still remaining on his Middlesbrough contract, but after two-and-a-half years of being out in the Riverside cold and enduring multiple loan moves away from the club, Stojanovic clearly felt that his chances of ever becoming a starting player in the North East were extremely slim.

Unfortunately, this was a transfer that just didn't work out for a multitude of reasons. Signings were routinely favoured over him, but in truth, Stojanovic never truly looked like a player who was ready to be entrusted with the starting gloves at Championship level in his rare Boro outings.