You have to go back to the dark days of the 1980s before the arrival of Graeme Souness for the last time Rangers lost four games on the spin.
And if it happens on Friday night then it's fair to say the honeymoon of title number 55 will be over – if it isn't already.
Steven Gerrard slumped to a third consecutive loss for the first time in his time in charge at Ibrox after they were sent spinning out of the Champions League by Malmo.
The Swedes inflicted defeats on Gers either side Dundee United's victory over the Light Blues at Tannadice.
Rangers have to dust themselves down and get back on track domestically and, on paper at least, they have the perfect opportunity.
Celtic legend Peter Grant will be relishing the prospect of trying to inflict more pain on Gers when he takes his Pars side to Govan.
But after a 3-0 defeat themselves to Partick Thistle in the Championship last time out then it's fair to say the odds are massively stacked against them.
However, the Light Blues are clearly vulnerable and depending on how they react the Fifers will be looking to do some damage and make sure it's their name in the hat for Sunday's quarter final draw.
When and where will the game take place?
The game takes place at the Ibrox Stadium on Friday, August 13 with a 7.30pm kick-off time.
What channel is it on?
The match will be shown live by tournament sponsors Premier Sports with coverage starting at 7pm.
Will there be a live stream?
Yes. You can stream the game to your device via the Premier Player website or app.
Where else can I follow the action?
You can keep up with all the action right here on dailyrecord.co.uk! We'll be running a live blog with all the pre-match build-up and team news, and every kick of the ball once the clash gets underway.
After the game, we'll have all the reaction from managers and players, as well as player ratings, talking points and a whole lot more.
