Former Chelsea Star Emerges As SHOCK Candidate For Vacant Middlesbrough Job

From Foxtrot to Top Job

Jimmy Floyd Hasselbaink has emerged as a surprise contender for the vacant Middlesbrough job, just weeks after his brief stint on Strictly Come Dancing. The 53-year-old Dutchman, partnered with Lauren Oakley, exited the competition last month, as the fourth celebrity eliminated.

Hasselbaink’s playing career remains etched in Premier League history. Arriving at Leeds United in 1997, he scored 22 goals in his debut season before a £15 million move to Chelsea in 2000. There, he won consecutive Premier League Golden Boots, netting 87 times in 177 appearances and powering the Blues to second place in 2003-04 and a Champions League semi-final.

His 23 caps for the Netherlands yielded 9 goals, while later spells at Cardiff City and Charlton Athletic added depth to a tally exceeding 245 goals across his impressive career. Crucially, he spent two seasons at Middlesbrough from 2004, scoring 18 goals in 70 games and starring in the club’s UEFA Cup final run in 2006 under Steve McClaren, a 4-0 defeat to Sevilla that still captures the imagination on Teeside.

On the touchline, Hasselbaink has shown his quality across the English Football League. Taking Burton Albion as player-manager in 2014, he secured promotion from League Two in his first full season and kept the Brewers in League One before departing in 2016 after 127 matches and a 38 per cent win rate.

At Northampton Town from 2017 to 2018, he inherited a fight at the bottom of the table, achieved survival, and pushed for playoffs across 84 games, winning 29. His direct, resilient style maximised modest squads, earning respect in the lower leagues for powerful and effective football.

Since 2023, he has served as an assistant to Sir Gareth Southgate with England, contributing to the Euro 2024 final and World Cup 2026 qualifiers. Working closely with world-class forwards like Harry Kane and Bukayo Saka, he has blended Dutch flair with English pragmatism, absorbing Southgate’s calm authority. Now, with Southgate gone, Hasselbaink stands ready for a head role back in the EFL.

How Might Hasselbaink’s Influence Help Boro in Their Hour of Need?

Middlesbrough began the Championship season under Rob Edwards with ambition. An opening draw at Swansea City was followed by wins over West Bromwich Albion, Ipswich Town, and Sheffield Wednesday. But by November, after 15 games, Boro sat 2nd with over 20 points. Draws against Southampton, Stoke City, Wrexham, and Leicester City, plus losses to Portsmouth and Watford, exposed fragility. Fans grew restless as summer promise faded.

Yesterday, a shockwave hit, Edwards left for Wolves in a £3 million deal, citing a “dream return” to Molineux.

His exit, just five months in, left Middlesbrough reeling. Assistant Adi Viveash guided a 2-1 win over Birmingham City, but the club urged unity amid chaos. Wolves, bottom of the Premier League with two points from 11, offered Edwards renewal which he could not turn down.

Hasselbaink fits like a glove. A former Boro striker, he knows the Riverside heartbeat, having scored in those UEFA Cup nights. His EFL grit suits the Championship grind, while England experience adds elite polish.

He could aim to sharpen Boro’s attack, mentor young forwards, and unify a now shaken squad. His homecoming narrative alone could reignite belief, yet a lack of Championship experience could prove the main problem.

Bookmakers favour others, but Hasselbaink lurks at 12/1. Below are the odds of the top 5 candidates per 5 of the biggest bookmakers in the country.