In February 2006, Jose Mourinho suffered the worst defeat of his Blues' reign to that point when thrashed 3-0 by the Teessiders.
Having taken charge in 2004, Mourinho had led Chelsea to the title in his first season with the Blues conceding just 15 goals all season. They seemed unstoppable.
Chelsea's XI that day included John Terry and Frank Lampard, as well as Arjen Robben, Hernan Crespo and Michael Essien.
They still won the league, but Mourinho had to sit through what was the joint heaviest defeat of his career to that point.
For Middlesbrough, things were far from rosy with manager Steve McClaren having an angry fan's season ticket thrown at him during a 4-0 defeat to Aston Villa, four days earlier.
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But goals from Fabio Rochemback, Stewart Downing and Yakubu Aiyegbeni completed a more-than deserved win.
Here's the Middlesbrough XI from that day - many of whom also played in a 4-1 hammering of Man United that ended the career of Roy Keane, who savaged his teammates in an in-house interview.
Mark Schwarzer (goalkeeper)
The goalkeeper was part of the furniture in the Premier League and spent 11 seasons with Middlesbrough before spending five years with Fulham.
Schwarzer enjoyed two years as a backup goalkeeper with Chelsea between 2013 and 2015 and won 109 caps as Australia's number one, representing them in the 2006 and 2010 World Cups.
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Stuart Parnaby (Right back)
An academy graduate, Parnaby was drafted in as a replacement for Abel Xavier who was serving a ban for failing a drugs test.
A right-back who could play centrally or in midfield, Parnaby made four appearances for England under-21 before injuries stopped him from fulfilling his potential.
Chris Riggott (centre back)
An England under-21 international who nearly joined Liverpool during the 2001/02 campaign, such was his level of promise as a youngster at Derby County.
Riggott became a regular defensive partner for Gareth Southgate and made 147 appearances for the club before injury saw his career derailed.
Gareth Southgate (centre back)
England's national team manager spent five years as a player with Middlesbrough, immediately being named captain and lifting the club's first major trophy - the League Cup - in their 128-year history.
The 2005/06 campaign was his last as a player after being fast-tracked into management as a replacement for the England-bound McClaren.
Emmanuel Pogatetz (left back)
Nicknamed 'Mad Dog', Pogatetz was handed a 24-week ban for inflicting a double-leg break on a player in Russia before joining Middlesbrough.
That ban was reduced to eight weeks when he joined with the no-nonsense defender being true to his reputation during his time at the club.
James Morrison (right midfielder)
Another academy graduate, Morrison made 66 appearances for Middlesbrough before spending the rest of his career at West Brom.
For Boro fans, though, his greatest moment was wiping out Cristiano Ronaldo for showboating during an FA Cup clash at Old Trafford where he received a straight-red card for his troubles.
Gaizka Mendieta (central midfielder)
An iconic figure in European football having captained Valencia in two Champions League finals in 2000 and 2001 and later represented Lazio, who made him the most expensive Spanish player at £29m in 2001 and then Barcelona in a glittering career.
His time at Middlesbrough, whom he initially joined on loan in 2003, saw moments of real quality along the way and scored twice in that infamous win over United, but now he gets his kicks by Djing to thousands at music festivals around the world - yes, really!
Doriva (central midfielder)
A no-nonsense Brazil international, Doriva enjoyed a hugely successful managerial career in Brazil after representing them as a player at the World Cup in 1998.
He now works as the assistant manager of Albania's national team.
Fabio Rochemback (central midfielder)
A Brazilian starlet who was signed by Barcelona in 2001 as the successor to Pep Guardiola, Rochemback spent two years at the Nou Camp before heading to Sporting Lisbon on a two-year loan deal.
The midfielder then joined Middlesbrough in 2005 and is best remembered for his 40-yard free-kick that rocketed into the top corner in an 8-1 victory over Man City.
Stewart Downing (left midfielder)
The crown jewel in Middlesbrough's academy crown, Downing made more than 400 appearances for the club during a career that also saw him represent Aston Villa, Liverpool and West Ham.
He has followed Mendieta into DJing and has been spotted spinning the decks everywhere from Middlesbrough to Ibiza.
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Yakubu Aiyegbeni (striker)
One of the Premier League's biggest cult heroes, Yakubu scored 35 goals for Portsmouth before joining Middlesbrough in 2005.
Joining forces with Mark Viduka and Jimmy Floyd Hasselbaink, the Nigeria international scored Boro's third against Chelsea with a fine solo effort, but left the club that summer to join Everton.