Andre Villas-Boas arrived at Stamford Bridge heralded as perhaps the most promising young manager in Europe, having led Porto to an unprecedented amount success domestically and on the continent.
Despite transforming Porto into Liga invincibles and claiming the Europa League, Villas-Boas' credentials to manage Chelsea were still questioned, due to his tender years - being aged only 33 at the time - and having yet to preside over a team in the Champions League.
The Portuguese was on a hiding to nothing from some quarters and, with Chelsea four points adrift of the Premier League's top four come early March, he was relieved of his duties after only 27 games as the club's manager.
Villas-Boas left Chelsea with a burgeoning reputation now damaged, as debriefs at the time revealed the full extent of how his almost dictatorial regime had disrupted the Blues' squad, and detailed his bizarre sleeping habits.
Appointing just him four months after his unceremonious Chelsea departure was certainly a risk for Tottenham, with Spurs having finished an impressive fourth the season before, but the faith installed in Villas-Boas by chairman Daniel Levy has proven a risk worth taking.
Villas-Boas has propelled Spurs into the Premier League's top three and, crucially, above former club Chelsea, as the Blues slide at an alarming rate under the stewardship of unpopular interim manager Rafael Benitez.
The 35-year-old former Porto boss can be forgiven for affording himself a wry smile at the plight of hisex-employers, with current form suggesting Villas-Boas led Spurs will strike a significant blow to Chelsea's position in English football come the end of the season.
Villas-Boas looks destined to get one over on Chelsea but he will not be the first, and certainly will not be the last, manager or player to come back to haunt their former club.
GMF highlights five similar instances over the years…
Denis Law's backheel adds to Manchester United's woes
Denis Law scored 237 goals in 11 seasons with Manchester United, forming part of the all-conquering Holy Trinity alongside fellow Old Trafford legends Bobby Charlton and George Best.
The Scottish forward did, however, play for rivals Manchester City either side of his stint with United, and scored a famous backheeled winner against his former club on the final day of the season in 1974.
Law chose not to celebrate the goal, thinking it had condemned Manchester United to relegation, and walked off the pitch with his head bowed when he was substituted almost immediately after.
Emmanuel Adebayor sticks the boot into Arsenal - and Robin van Persie
Tensions were already running high before Arsenal travelled to the Etihad Stadium in September of 2009, with Gunners fans still infuriated with former striker Emmanuel Adebayor having forced a transfer to Manchester City that summer.
The Togolese was the subject of vociferous objection from the away support for the entirety of the encounter and, when he inevitably found the net, ran the length of the field to goad the Arsenal fans.
City won 4-2 on the day, but Adebayor later received a three-match ban retrospectively having been deemed to deliberately kick Arsenal striker Robin van Persie in the face.
Jose Mourinho leads Inter to a special two against Chelsea
Given Roman Abromovich's notoriously itchy trigger finger, it comes as no real surprise that his decisions have a habit of coming back to bite him on the posterior.
Jose Mourinho did just that, not literally of course, when he faced Chelsea for the first time since he left Stamford Bridge in shock circumstances in September of 2007.
The Special One led Inter Milan to victories at the San Siro and Stamford Bridge in the two-legged Champions League last 16 tie, and the Portuguese went on to claim the competition for the second time in his career.
Sol Campbell wins the league at White Hart Lane
Sol Campbell is a player who will forever divide north London - formerly loved at Tottenham before adulation turned to vitriol when the centre-back decided to sign for Arsenal after his contract at White Hart Lane had expired.
The former England international was in his third season at Arsenal when they travelled to Spurs knowing a point would be enough to secure the title ahead of rivals Chelsea and Manchester United.
Arsenal got the result required with the score finishing 2-2, and Campbell was able to claim a the league title in front of the fans who harboured hatred to their respective cores.
Cristiano Ronaldo ends Manchester United's Champions League hopes?
Cristiano Ronaldo returns to Old Trafford for the first time as a Real Madrid player on Tuesday night, and the stage is set for the Portuguese to ruin Manchester United's chances of Champions League progression.
The tie is delicately poised after the first leg at the Santiago Bernabeu, with Ronaldo have cancelled out Danny Welbeck's opener for Manchester United on the night.
Ronaldo says he would 'love' to score against his former club, and few would bet against the Real Madrid star playing an instrumental role at the Theatre of Dreams.