Steve Lomas was sacked by Millwall following a Boxing Day 4-0 defeat to Watford, and Holloway, with his successful promotion record, was appointed to turn the season around, and save the club from the relegation which had threatened for the duration of Lomas' tenure.
Unfortunately for Holloway, is has not gone to plan. Recording only three victories since his arrival, the club linger second from bottom, two points off Charlton Athletic in 21st who also have two games in hand on their relegation rivals.
For all the negativity surrounding the current situation at The New Den, a 2-1 victory away at Nottingham Forest could potentially kick start the run of form needed to survive in the Championship.
Scott Malone and Lee Martin secured the points for Millwall, with caretaker Gary Brazil struggling to revive the fortunes of the fading Forest side. A run of 10 games without victory have left Forest outside of the playoff places, and resulted in the sacking of acerbic manager Billy Davies.
Although Forest favourite Stuart Pearce has been confirmed as taking the role, it will not be until next season - a season likely to be in the Championship.
Although their early season form has secured their survival, Forest are currently in a worse run of form than Millwall, and both clubs are trudging through their final games with a sense of despair.
Whilst it appears that Forest are now out of any potential promotion, Millwall still have their survival to play for, and Holloway believes he can achieve the results needed for another season in the second tier of English football.
Before the Forest game, Holloway insisted to Sky Sports, "We've still got a chance.
"We have to get five wins from our last seven games. There are two tough away matches coming up against Forest and Wigan, but we went to Derby and got a win so why can't we do it again?"
He managed to stay true to his word and record success over Forest, stepping closer to safety, and with the confidence victory should have bestowed upon his team, the upcoming matches offer a real chance to secure survival.
Tuesday sees Millwall travel to current FA Cup holders Wigan. While Wigan have arguably the strongest squad in the Championship, they have suffered in recent weeks; draws to Yeovil and Bolton came as surprises, although Saturday's victory over Leeds appears to have recalled their earlier form.
A second consecutive away victory would do wonders for Millwall, and Holloway is adamant he can achieve it. Whilst unlikely on comparison of their respective squads, the Championship is host to enough upsets for teams to be wary of so-called 'weaker' opposition, and Holloway has enough experience of the division to understand this.