Some of the deals that have been conducted involve obligations and options to buy, it yet to be seen whether those transfers will be made permanent.
Nevertheless, at a time when Mauricio Pochettino has not been shy in including academy prospects and youngsters acquired from elsewhere on his substitutes' bench, attention is being paid to how players are faring elsewhere, either from a development or financial perspective.
Here, Sports Mole takes a look at each of the respective situations, assessing whether they can be regarded as a success or failure at this stage.
FOREIGN LOANS
Having only been provided with 409 minutes of football spread across 15 appearances by Pochettino, Ian Maatsen has immediately gone on to make seven starts at Borussia Dortmund in the Bundesliga and Champions League.
Whether the German giants activate a £35m buy option remains to be seen, but there may be room for manoeuvre on Chelsea's side if it means cashing in on the left-sided Dutch player.
Young Brazilian Angelo has been one of the success stories so far, the 19-year-old featuring for 999 minutes across 20 Ligue 1 outings while at Strasbourg, contributing three assists in the process.
He has since been joined by compatriot Andrey Santos, who made his debut from the substitutes' bench at the weekend, while American goalkeeper Gabriel Slonina has made 24 starts for Eupen in the Belgian top flight.
Galatasaray will sign Hakim Ziyech on a permanent basis at the end of the season, although the Morocco international has made just nine starts and five substitute outings in Super Lig and Champions League fixtures.
Kepa Arrizabalaga has recently lost his place in the team at Real Madrid after making 18 starts, the likelihood now being that he will return to Chelsea at the end of the season with one year left on his contract.
Unless Roma can negotiate a permanent deal, the same will likely apply to Romelu Lukaku, who has scored 16 goals for the Italian outfit in all competitions and holds a contract at Chelsea until 2026.
DOMESTIC LOANS
Chelsea loaned Armando Broja to Fulham in the hope that he would receive regular game time. Instead, the form of Rodrigo Muniz has led to the forward featuring for just 32 minutes across two substitute outings.
As it stands, Fulham look likely to pay Chelsea a loan fee for failing to use Broja frequently enough, but the Blues will be delighted with David Datro Fofana's game time at Burnley.
Two goals and one assist have come from 238 minutes of Premier League football, already more than Lewis Hall has acquired all season at Newcastle United.
Terms are in place for the Magpies to buy the youngster in the summer, yet it is unclear whether Hall making just four starts and seven substitute outings is enough to activate that £28m clause.
In the Championship, Mason Burstow has contributed just one goal and one assist from his 11 starts and six substitute outings for Sunderland under three different managers.
Defender Bashir Humphreys has 25 appearances to his name at a struggling Swansea City, while Alex Matos has already made seven Championship starts for Huddersfield Town since moving to the Terriers in January.
Omari Hutchinson continues to impress at Championship promotion contenders Ipswich Town, making 14 starts and 23 substitute outings in all competitions that have led to five goals and five assists.
In League One, Harvey Vale has emerged as a key man for Bristol Rovers, chipping in with two goals and four assists from 28 league appearances, largely from the left flank.
Injury has restricted Tino Anjorin to four starts and four substitute outings at Portsmouth, the playmaker not featuring since November, while Dion Rankine has accumulated 18 starts and six substitute outings for Exeter City in the third tier, predominantly down the right-hand side.
Goalkeeper Jamie Cumming, who has spent time on the Chelsea substitutes' bench this season, has made eight starts for Oxford United since his January move, but Zak Sturge's loan at Peterborough United has not worked out with the left-sided player making two starts and 10 substitute outings, as well as not featuring since December.
ACADEMY LOANS
Although Charlie Webster has gained valuable experience with Dutch side Heerenveen, the midfielder has been given just 119 minutes across seven Eredivisie appearances, the most recent coming in January.
Goalkeeper Teddy Sharman-Lowe has made just one appearance during his season-long loan stint with National League side Bromley, but Eddie Beach is faring much better at Gateshead, conceding just seven goals in four appearances since his January loan switch.