One of the best strikers of his era, Jimmy Floyd Hasselbaink played an instrumental role in our first two seasons in the Uefa Cup.
He joined Boro on a free transfer from Chelsea in July 2004, one day after fellow forward Mark Viduka put pen to paper on a Teesside move.
He firmly established himself as one of the best clinical strikers around following successful spells with Leeds United, Atletico Madrid and his four-year stay at Stamford Bridge.
Hasselbaink has a special place in Boro folklore having netted our first-ever European goal, which came in the 3-0 victory over Banjk Ostrava at the Riverside.
He found the back of the net 16 times during his first season on Teesside, making him our top scorer during the 2004/05 season.
The former Holland international chalked up another impressive goal haul in his second season of 18, with more memorable goals on the European stage.
He scored in the second leg against Roma, which helped us reach the quarter-finals of the Uefa Cup, before unleashing a stunning strike in the memorable comeback win against FC Basel.
Boro reached the Uefa Cup final in his last campaign on Teesside, with the final against Sevilla his last appearance for us, departing with 34 goals in 89 games.
He headed back to London to link up with Charlton Athletic before finishing his playing career with Cardiff City, with whom he helped beat Boro on their way to the FA Cup final.
After hanging his boots up in 2008, Hasselbaink moved into coaching and secured his first management job with Royal Antwerp.
He then took over the managerial reins at Burton Albion, steering the Brewers to the League Two title.
Hasselbaink had further managerial stints at Queens Park Rangers and Northampton Town.