Emmanuel Adebayor is not only on a red-hot goalscoring streak, he also has three goals in his last four Premier League starts against the Blues.
The Togolese hitman has plundered a respectable 11 goals from 16 games since Sherwood took the reins from Andre Villas-Boas and has appeared revitalised under new stewardship, having failed to find the back of the net since May prior to his strike in the League Cup loss to West Ham United.
His goals have been crucial and eye-catching in equal measure, particularly in matchwinning cameos against Southampton, Swansea, Manchester United and Everton.
The last was most pertinent in that it has given Tottenham breathing space in fifth place and keeps them on the coat-tails of fourth place, which would provide Champions League football, albeit with a qualifier to navigate through first.
Having been denied by late season surges from North London rivals and Adebayor's former employers Arsenal in recent seasons, there will be extra motivation for the recently-turned 30-year-old.
He has kept Spurs' Europa League adventure alive too, after his deadly brace against Dnipro led his side into the round of 16 and now he is tasked with arguably his biggest test yet since his renaissance took off.
Adebayor should not be fazed by the task in hand, however, given his recent record against Chelsea, who Spurs travel to for the teatime clash on Saturday.
It may seem more daunting by the crippling injury list which has deprived Sherwood of the likes of Christian Eriksen, Danny Rose, Vlad Chiriches, Etienne Capoue and Erik Lamela.
There are also lingering doubts over Kyle Walker so the prospect of Kyle Naughton and Zeki Fryers coming up against a rampant Eden Hazard and Andre Schürrle is enough to send a chill down the spine of Spurs supporters but they should keep faith for, if any reason, Adebayor's recent record against the Blues.
His strike rate of three goals in his last four Premier League starts versus the west London outfit - two for Spurs, one for Manchester City - is prolific and given his recent barnstorming goalscoring run, even the water-tight defensive duo of John Terry and Gary Cahill face a gruelling contest at the hands of the rangy striker.
Roberto Soldado's toils have been well documented but even he got himself on the scoresheet against Cardiff City last weekend. Spurs will be hoping Adebayor's personal history in this fixture can put an end to a testing one of their own, having endured 24 years' worth of winless visits to Stamford Bridge for the club.
image: © Roger Gorączniak