Chelsea will be bidding to extend a 13-year streak when they face Atalanta BC on Tuesday night.
The Premier League and Serie A sides meet in Italy with both clubs sitting on 10 points in the League Phase of the Champions League.
With just three games remaining, victory will guarantee a top-24 spot and strengthen either side's attempt to finish inside the top eight, subsequently earning a place in the last 16 of the competition.
Despite defeat to Hellas Verona at the weekend, Atalanta have won three of their last five outings, while Chelsea are without success in their most recent three contests.
Furthermore, it is the West Londoners who are under pressure to avoid ending a 13-year run of results when they take to the pitch in Bergamo.
Chelsea at risk of ending Champions League streak
Under different managers, Chelsea have failed to win any of their last four away fixtures in the Champions League.
As well as a 2-2 draw at Azerbaijani side Qarabag FK in their last such fixture, defeats have been posted at Borussia Dortmund, Real Madrid and Bayern Munich.
If Chelsea fail to emerge victorious on Tuesday, it will represent the first time since 2012 that they have gone five consecutive away matches in the competition without success.
Meanwhile, Enzo Maresca is hoping to avoid becoming just the third Chelsea manger - the others being Luiz Felipe Scolari and Andre Villas-Boas - to not win any of their first three Champions League away fixtures in charge of the club.
Chelsea's dismal record in Italy
Tuesday's game will represent Chelsea's 12th away fixture against Italian opposition in the Champions League. However, they have won just twice.
Their first such triumph came in 2004 when they thrashed Lazio by a 4-0 scoreline, while they also prevailed from their last such encounter - at AC Milan in October 2022 - with a 2-0 win.
Three draws and six defeats have been registered in the other encounters, the stalemates coming at AC Milan and Lazio in 1999-2000, as well as Juventus in 2008-09.
Between 2009-10 and 2021-22, Chelsea suffered five consecutive defeats in Champions League fixtures in Italy.