Having conceded 11 goals across two games with Manchester City and slumping to a 5-0 home defeat to Liverpool, heavy thrashings at the hands of the Premier League's leading lights have become an unwanted feature of Tottenham's season.
They held their own for 54 minutes at Stamford Bridge on Saturday before Jan Vertonghen's slip and subsequently ill-judged pass allowed Samuel Eto'o to open the scoring.
Younes Kaboul was sent off for a foul on Eto'o and Eden Hazard converted the penalty before substitute Demba Ba benefited from two more late moments of Tottenham generosity.
It was the latter goals that truly riled Sherwood and in an interview with Sky Sports he bemoaned a "lack of characters" in his squad - a theme he picked up at the post-match press conference.
Asked for his thoughts on the frequency of such collapses, he said: "(It happens) too often, too often and again today against the big sides. It's disappointing to see.
"You're 2-0 down with 10 men at Chelsea, you're not going to win the game. But I expect to see a little more gut, a little bit more pride, a little bit more feather rustling.
"I don't want to be the only one who ever shouts at them. I think they need to dig each other out every now and again and get the best out of each other.
"It's on to the next now, we play Benfica on Thursday (in the UEFA Europa League).
"We haven't got time to dwell on this now but I'm gutted, massively disappointed - not too much about the result and the performance in the first half but the capitulation which the team showed and have showed too often this season."
Although his own team's failings were Sherwood's primary focus, he did query the decision from referee Michael Oliver to award a 60th-minute penalty and dismiss Kaboul.
"I appreciate that referees have got a very tough job and they've got to make that call but it could well have gone against us that one," he added.
"I think it's a soft decision because I think it's not a penalty. Obviously the sending off comes with it.
"We'll have to look at it a few more times. It’s a shame the referee doesn’t get that opportunity."
