Hakim Ziyech and Christian Pulisic could have left Chelsea last summer as part of a swap deal that included AC Milan star Rafael Leao moving in the opposite direction.
Co-owners Todd Boehly and Behdad Eghbali were in the midst of their first transfer window and submitted a proposal to Milan for Portugal international Leao. The Blues valued the 23-year-old at £87million but wished to include players in exchange to reduce the cash fee and make up the overall package.
According to The Athletic, Chelsea offered Ziyech and Pulisic to Milan, but their bid was quickly rejected as the Rossoneri were not convinced. They felt the Blues showed interest too late in the transfer window and pointed to the £130m release clause Leao had in his contract instead, which Boehly and Eghbali were not prepared to buy out.
Four months later, Chelsea went back in for Leao after he impressed in both Champions League matches against the Blues earlier in the season. But, once again, they were unable to secure Leao's services. Then-manager Graham Potter decided to sign Mykhaylo Mudryk in a £87m deal instead.
After the end of the January window, Chelsea attempted again to have a look at Leao's situation and future, with his contract slowly running out. However, the Blues are likely to miss out on the attacker for the third window in a row after he committed his future to Milan by signing a five-year deal.
Chelsea are now going to have to look elsewhere for attacking targets this summer as incoming boss Mauricio Pochettino tries to bolster their forward line. The Blues have struggled for goals this season, scoring a mere 36 in 35 matches, fewer than relegation-threatened Leeds and Leicester.
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Romelu Lukaku is set to return to Chelsea following his loan spell at Inter Milan, but his future is uncertain and the Blues are still likely to dip into the market. Harry Kane has been linked with a reunion with former boss Pochettino, while the likes of Napoli's Victor Osimhen and Brentford's Ivan Toney have also been tipped to join the Blues.
As for Chelsea's current predicament, interim manager Frank Lampard has won just one of his opening eight matches in charge and the Blues were held to a 2-2 draw against Nottingham Forest on Sunday. Speaking after the game, Lampard insisted Chelsea must improve.
He said: "The second half was ours, control of the game was ours, obviously, in terms of possession, but in the first half we weren't dynamic enough in the top end of the pitch.
"Everything we spoke about at the start of the game, it was too slow. Unfortunately, it seems to be intrinsic here at the minute where we play a lot of passes but they are not to break lines or to threaten the opposition in the top end of the pitch."
