Their next Premier League fixture is not until April 12th, but the clash with Manchester City will spark a decisive run that determines whether Rosenior oversees their summer business.
Official word out of Stamford Bridge suggests the head coach is not under pressure, yet sources have told Flashscore that his position will be on the line if results continue to decline.
Chelsea insist they are not placing personal blame on Rosenior for the current run of four consecutive defeats, during which the team have failed to score in the last three games.
However, there is an understanding that performances must improve, particularly given that Champions League qualification was a primary objective at the start of the season.
That target remains within reach, but Chelsea are currently sixth, and another loss would allow Brentford and Everton to overtake them in the league standings.
Although Rosenior signed a six-year contract, it is understood that his role is not guaranteed for next season if this term spirals.
Chelsea’s hierarchy want the project to succeed, but they are also planning to invest significantly again in the summer transfer market, so they need full faith in the direction under Rosenior if he is to remain at the helm.
Signing a top-level centre-back is a real possibility, while the club are also considering reinforcements in goal, midfield and attack. Ultimately, this raises a broader decision about whether they believe in the core of the current squad.
There is also the possibility that Chelsea target one or two players with greater pedigree than in recent windows, suggesting a shift towards a more “win-now” approach rather than focusing on long-term development.
But first, they need to address this season's issues on the pitch. An FA Cup quarter-final against Port Vale offers hope of silverware, but in the Premier League, a demanding schedule will require significant improvement.
The clash with Man City is followed by a meeting with Manchester United, before a trip to Brighton - one of the most in-form teams in the league. Chelsea then face Nottingham Forest, who are battling to stay in the division, before travelling to Anfield to take on Liverpool.
Each of these fixtures presents a different challenge, and if Rosenior cannot find solutions before Chelsea head into their final games against Tottenham and Sunderland, he will be in trouble.
With a major summer outlay planned, the games may prove decisive in whether Chelsea entrust Rosenior with the next phase of the rebuild.
