Roman Abramovich's reign at Stamford Bridge is about to come to an end, with the Russian having delivered 19 trophies in 21 years. Daniel Levy, meanwhile, has been at the helm at Spurs for a similar amount of time and has only got one piece of silverware to show for it - and that was the League Cup.
The disparity in the trophy cabinets is not the only contrasting features from their spells in north and west London as Planet Sport finds out.
How did the two take over?
Russian billionaire Abramovich made his money through selling previously state-owned assets he acquired following the collapse of the Soviet Union.
Abramovich bought Chelsea off Ken Bates for an overall fee of around £140million in 2003. This was effectively pocket money for Abramovich who, in 2019, had a reported worth of over $12.9billion, according to Forbes.
Businessman Levy, meanwhile, was appointed to Spurs' board in 2000 after ENIC (a company he has a large share in) took over, purchasing 29.9% of the club from Lord Alan Sugar.
Billionaire investor Joe Lewis owns the majority of the club, with Levy, 29.4% of the share capital of ENIC, chairman.
In the years since acquiring the majority share, ENIC increased their shareholding and now own 85.55% of the north London club.
Managers employed by Levy and Abramovich
Ten have come and gone for Daniel Levy, who is the longest-serving chairman in the Premier League, starting with Glenn Hoddle.
Levy has gone through a manager just shy of every two years, but with uncertainty already surrounding 11th boss Antonio Conte, that average could soon take a hit.
In recent times, high-profile appointments including Jose Mourinho and Mauricio Pochettino have failed to deliver the success the club crave, with the biggest flop being Frenchman Jaques Santini who lasted a mere 13 games.
Chelsea have seen 13 managers take charge of five or more matches since Roman took over in 2003. The list of ex-bosses also includes Mourinho (twice) and Andre Villas-Boas, with the popular Thomas Tuchel the current incumbent.
Trophies won by Levy and Abramovich
Tottenham fans should look away now. Levy has overseen Spurs lift a grand total of one trophy, the League Cup back in 2008 where they defeated Chelsea 2-1 at Wembley courtesy of a Jonathan Woodgate winner.
Spurs extended their trophyless run to 14 years recently when they were knocked out of the FA Cup by Championship side Middlesbrough.
Chelsea, in contrast, are the Premier League's winningest team in terms of trophies since the Abramovich era started. The Blues boast 19 trophies since 2003, putting them level with Manchester United. Those include the Champions League (2), FA Cup (5), Premier League (5) and most recently the FIFA Club World Cup.
Money spent under Levy and Abramovich
Unsurprisingly, Abramovich has ploughed more money into the club in the search of success, spending more than £2billion.
The Russian's first transfer window laid down a marker for those that would follow, with £100 million spent. His second summer window saw £94million shelled out, giving Mourinho the platform to win back-to-back league titles in 2004/05 and 2005/06.
Belgian striker Romelu Lukaku tops the list for their most expensive purchase, bought for a fee of around £100million to start a second spell at the club. Six other players joined the Blues for over £50million, including the disastrous captures of Spaniard's Fernando Torres and Alvaro Morata.
Over the past three seasons alone, Tottenham Hotspur have spent £320million, with Bryan Gil and Tanguy Ndombele having both since left the club on loan deals.
Since the 2012/13 campaign, Levy has spent £790million on players, with very only four top-four finishes and a Champions League final to show for it.
Notable signings in the past decade include Hugo Lloris (2012), Heung-min Son (2015) and Dele Alli (also 2015) but flops including Vincent Janssen and Moussa Sissoko (both 2016) and Roberto Soldado (2013) certainly outweigh the successful buys.
How much money has been put in?
Roman Abramovich is reported to have pumped over £1.5billion into the club since 2003. However, after putting the club up for sale, he says he is prepared to write off that money.
Tottenham, meanwhile, have a reputation for frugality and it is difficult to put an exact figure on the amount that has been invested into the club.
The Tottenham Hotspur Stadium, opened in 2019 and has a complete cost of £1billion but owners ENIC have only contributed a small amount of that figure after loaning £637 million from Goldman Sachs, Bank of America Merrill Lynch and HSBC. It is yet to be seen how much of that figure has been repaid.
Unwilling to bankroll the club to the extent of Abramovich, Tottenham have had to rely on Levy's reputation as a stubborn negotiator. That stubbornness was reflected when Man City reportedly had multiple bids for Harry Kane turned down in the summer, despite the England striker desperate to leave the club.
But while hanging onto Kane was a major coup, the reason he wanted to leave in the first place is still the biggest disparity between Abramovich's and Levy's reigns - he wanted to win trophies and he'll never do that while at Spurs.