He has a much tougher task on his hands this time around. Burton are rock bottom of League One and eight points from safety.
Here is our preview of their matchup against Gillingham this weekend.
Goalkeeper Joe Walsh is back available for selection after a period of self-isolation, and he is expected to resume as understudy to Jack Bonham.
Jacob Mellis could be fit, but the match is expected to be slightly too soon for midfielder Stuart O’Keefe, who, after breaking his leg in September, has now resumed full training.
For Burton, Hayden Carter is expected to feature after signing on loan from Blackburn Rovers earlier in the week.
Niall Ennis, however, will not play a part after returning from his loan spell to parent club Wolves.
Hasselbaink is expected to make wholesale changes to the starting 11 after the Brewers were hammered 5-1 at home against Oxford United last weekend.
Gillingham (possible 442): Bonham - Jackson, Tucker, Ogilvie, O’Connor - Graham, McKenzie, Dempsey, Johnson - Oliver, Akinde.
Burton (possible 4-2-3-1): O’Hara - Brayford, Bostwick, Carter, Daniels - Edwards, Quinn - Atkins, Powell, Vernam - Hemmings.
After a positive run of form, Gillingham have now suffered four defeats from their last five games in League One. Their only win in the run came on December 29 away to Rochdale (4-1), and they have lost their last two; 3-1 and 1-0 to Northampton Town and Plymouth Argyle respectively.
They are 14th in the league table and six points off the play-off spots.
Burton are in dire form. They are rock bottom of League One and have just two wins to their names from 22 matches this campaign.
They have lost their last five games have and no win in eight - their poor form resulting in the club parting ways with manager Jake Buxton just before the turn of the new year.
The Brewers are eight points from safety, and the new management team will be hoping to start their survival mission in a positive manner on Saturday.
Ones to watch
There is little doubt that Jordan Graham is the one to watch for Gillingham. The winger played 90 minutes at Plymouth after missing seven games with a hamstring injury, and has notched five goals and three assists from his 14 league appearances so far this season.
The former Wolves man adds width and pace to Gillingham’s attack, and will be vital to helping his side out of their poor run of form.
Burton haven’t really struggled to score goals this season - in fact 14 teams in the division have scored fewer than the Brewers’ 28 - but they have leaked goals at will at the back.
Their 50 goals conceded is nine more than any other team, and Hasselbaink has made keeping clean sheets his top priority.
That said, forward Kane Hemmings has been in fine form this season, netting eight goals from 18 appearances. He is worth keeping an eye on.
The last time the two teams met was on February 8 2020, which saw a 0-0 draw at the Pirelli Stadium. Burton won last year’s reverse fixture, however, as a Nathan Broadhead double cancelled out Ouss Cisse’s opener at Priestfield in August.
In total, the teams have crossed paths 14 times in their histories. Gillingham lead the way in terms of wins with six victories to Burton’s three, whilst there have also been five draws between the two sides.
How to watch
The game has not been selected for TV coverage in the UK, but an iFollow pass can be purchased for £10 via either club’s website to stream the game live.
Gillingham season ticket holders can watch for free. Kick-off is scheduled for 14:00 BST.
What they’ve said
Gills assistant manager Paul Raynor was wary of the “wounded animal” of Burton when talking to the press on Thursday.
He said: “The challenge is the new manager going in. Jimmy has been there before and will know a lot of the guys and what buttons to push. He is a very knowledgeable guy.
“We have looked at the squad and the calibre of players at his disposal and there is a potential for a good side there. We are taking nothing for granted – football is not played on paper.
“I am sure the new manager will get a response. They are in a bit of a rut with performances and results, but they are a wounded animal, and it is going to be a tough game.”
Jimmy Floyd Hasselbaink was pleased with his team’s application since he took over when speaking to Burton’s club website in the week.
He said: “The application of the players has been great. Hard work - they have been giving me what they have got.
“Their reaction has been good - Monday, Tuesday and Wednesday were tough, but I am happy.”