Sunday's 1-0 loss to Corinthians in the Club World Cup final in Japan came 12 days after Chelsea's defence of the Champions League was cut short by an unprecedented elimination at the group stage.
Chelsea also lost 4-1 to Atletico Madrid in the UEFA Super Cup in August and was beaten 3-2 by Manchester City in the Community Shield weeks earlier, meaning four opportunities for silverware have already slipped by.
When the squad returns on a 12-hour, 6,000-mile flight from the Far East, a tough-looking schedule of six matches in 17 days awaits — starting with a League Cup quarterfinal against second-tier Leeds on Wednesday before games in the FA Cup and Premier League.
It promises to be a defining period for the London club and its embattled interim manager Rafael Benitez.
"We now have to go on a run of games in the league to keep ourselves in the hunt and we have the FA Cup and League Cup as well," Chelsea midfielder Frank Lampard said, "so we have to keep pushing on."
Chelsea is already 13 points behind Premier League leader Manchester United, so the League Cup may be Benitez's best chance of silverware in his brief tenure this season.
The team also has the Europa League to contest but after the highs of winning the Champions League in Munich in May, it is some fall from grace.
For an owner as ambitious and demanding as Russian billionaire Roman Abramovich, this latest setback — coming in front of a global audience — will hurt.
Chelsea became the first European champions to fail to win the Club World Cup since 2006 after a tired performance against Corinthians, which ended in further misery when Gary Cahill was sent off in the last minute.
"It's a tough moment, especially for the Chelsea fans that came to Japan," Chelsea midfielder Juan Mata said.
"I hope we can enjoy good moments and lift more trophies for the club ... very soon. We're still playing to win four trophies and we will give everything we have to success in each of them."
Benitez is likely to face more criticism from fans this week, particularly if the after-effects of the draining trip to Japan take in a surprise loss to Leeds at Elland Road.
Fernando Torres still looks like a striker lacking confidence, despite scoring five goals in three matches before Sunday's game, while supporters will wonder why Lampard and Ashley Cole appear set to leave the club in June at the end of their contracts.
However, it's not all doom and gloom for Benitez.
Captain John Terry is ready to return from a knee injury that has kept him out since Nov. 11 while the Spanish coach appears to have stumbled upon the best way to utilize the undoubted talent of another centre back, David Luiz.
The mercurial Brazil international looked more at home in centre midfield in the 3-1 win over Monterrey in the Club World Cup semifinal than he did in central defence in the final.
With holding midfielder John Obi Mikel set to miss the match at Leeds and also the league game against Aston Villa on Sunday through suspension, Luiz may have more chances to show his adaptability in a new position.
For now, though, an inconsolable Luiz must recover from losing Sunday's final to a team from his native country.
"I have a heavy heart," said Luiz, who left the field in Yokohama in tears. "I am disappointed but I need to look to the future because I have many games ahead. I play for a big club and I need to win big titles."