Jonathan Woodgate paid £1 million to bring Austrian custodian Dejan Stojanovic to Middlesbrough in January 2020, hoping that he would replace Darren Randolph.
Stojanovic was signed just one day after the Irish shot stopper left Riverside to join Premier League club West Ham United for an estimated £4 million.
With Middlesbrough’s starting gloves suddenly up for grabs, the Austrian custodian appeared to be the obvious choice, and with an eight-figure amount paid to bring him to Teesside, expectations were high.
Stojanovic, on the other hand, had a dismal two-and-a-half years in the North East, leaving a legacy as one of the club’s most perplexing signings in recent years.
Stojanovic fails to take the starting position from Aynsley Pears.
Randolph had apparently been suffering from a quad muscle ailment since early November 2019, allowing Middlesbrough academy graduate Aynsley Pears to compete for the starting spot.
His only previous senior experience had come from loan spells with non-league clubs Gateshead and Darlington, but Woodgate clearly believed the young custodian was ready to make the step up to the Championship.
Pears went on to make 25 appearances for Boro during the 2019/20 season, limiting Stojanovic to only eight in his first few months as a Middlesbrough player.
Neil Warnock prefers Marcus Bettinelli above Stojanovic.
However, in the summer of 2020, Woodgate was fired as Middlesbrough manager and replaced by Neil Warnock.
Could this managerial shift provide Stojanovic a fresh start at the Riverside? The answer to that inquiry was quick and simple: no. Warnock recruited Fulham custodian Marcus Bettinelli on a season-long loan in September of that year, and he soon established himself as Boro’s new first choice.
This meant that Pears had been demoted to the number two spot, which, after proving himself ready to start in the Championship, was not a role he was willing to play. As a result, he left the club permanently in October, signing for Blackburn Rovers instead.
Stojanovic was suddenly pushed up the depth chart, but Bettinelli was not about to go in-between the sticks, and by January 2021, the Austrian had only made one appearance for Boro in the EFL Cup that season.
As a result, he and the club decided that a loan move away from the club would be best for him at the time, and he signed with then-German second division side St.
Pauli on a temporary agreement until the conclusion of the 20/21 season. Stojanovic leaves after being the third-choice keeper behind Joe Lumley and Luke Daniels.
Stojanovic would return to the North East in the summer of 2021, and with Bettinelli and Jordan Archer also returning to their parent clubs, it felt that now was his greatest chance of establishing himself as a starter at Riverside.
After all, he appeared to have a reasonably easy path to the number one spot, until Warnock made a slew of goalkeeping signings. Joe Lumley signed on a free transfer from QPR, and experienced shot stopper Luke Daniels joined on a free transfer from Brentford.
Stojanovic’s best opportunity of becoming Middlesbrough’s number one since joining the club vanished in an instant, as Lumley took Warnock’s starting gloves.
Despite a mistake-filled season, he was able to retain his job in the Boro starting lineup, and when Warnock rotated, Daniels was chosen over Stojanovic.
So, when the January transfer window rolled around in 2022, Boro’s Austrian found himself on loan again after failing to make a single appearance that season. He returned to the German second tier, this time signing with Ingolstadt until the conclusion of the season.
Stojanovic, who had not featured for Boro since September 2020, ended his pretty catastrophic Middlesbrough career in the summer of 2022 when he joined German second division team SSV Jahn Regensburg.
He did so with one year remaining on his Middlesbrough contract, but after two and a half years away from the Riverside and multiple loan moves, Stojanovic clearly believed that his chances of ever becoming a starting player in the North East were slim. Unfortunately, this was not a successful transfer for a variety of reasons.
Stojanovic was often overshadowed by new signings, but in his few Boro appearances, he never looked like a player fit to start in the Championship.
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