The 18-year-old had travelled with the Blues squad up to Leicester but didn’t play and wasn’t even on the bench.
Not the most exhilarating of afternoons for the teenager. By the time it ended, however, Gilmour’s head was in a spin.
Billy Gilmour had a watershed moment in a Chelsea shirt in the FA Cup win against Liverpool
The Scottish teenager was the man of the match and showed his ability to dominate midfield
Lampard had a quiet word in the youngster’s ear as they returned to London that day, informing the midfielder that once the players returned from their winter break he would remain permanently with the first-team squad.
Music to any academy graduate’s ears and Gilmour was no different. All those years of graft and sacrifice — leaving his family home in Ardrossan at the age of 15 to pursue his Premier League dream — was suddenly worth it.
It wasn’t like he was going nowhere in Rangers’ academy. He was viewed as one of their most exciting prospects in the past 20 years.
Then Rangers boss Pedro Caixinha intervened in a bid to ensure he remained at Ibrox, but to no avail. Even the SFA’s performance director Malky Mackay advised Gilmour to stay, believing he’d have a better chance of breaking into senior football north of the border.
However, Gilmour would not listen. He wanted more. He knows he is good enough — and his incredible performance against Liverpool in the FA Cup on Tuesday night was proof of his immeasurable talent. At complete ease with the ball at his feet, it’s no wonder he’s already been dubbed the Scottish Xavi.
The fact Gilmour stands at just 5ft 6ins makes no bones to Lampard, who privately believes the youngster’s passing, vision and ball retention is as good — if not better — than anyone in his squad.
Frank Lampard has integrated Gilmour into the first-team squad and is nurturing him closely
‘I’ve got absolute trust in Billy. If he is small in stature, he is huge in personality and talent,’ said Lampard after watching Gilmour pull the strings against Liverpool.
Gilmour is no stranger to the limelight. Away from football, he has modelled for fashion house Burberry. But it’s his strides on the pitch, rather than the catwalk, that can catapult him to stardom.
There’s plenty to learn, of course. He is yet to make his first Premier League start. And, with Chelsea clinging on to a top-four place by their fingertips, you wonder if Lampard will risk Gilmour with so much at stake. It’s all part of a learning curve.
Much like his encounter with Harry Maguire during the EFL Cup defeat to Manchester United at Stamford Bridge in October.
‘He was pushing me off, gripping me by the throat. Basically, he was saying I’m a wee guy,’ recalled Gilmour, who started in the game against United.
‘That’s something I have to deal with. But I won’t let that happen again. That was a lesson. He is going to try to bully young ones and that’s where I need to learn how to be stronger.
Gilmour’s ambition showed no limit as he left Rangers to try his luck in England with Chelsea
The teenager’s composure was most impressive against Liverpool at Stamford Bridge
‘I’ve been working on that and I can only get stronger. But that was a learning curve when he gripped me in the box.’
Gilmour has not been put off by that bruising confrontation with United’s captain, certainly judging by Tuesday night’s swaggering performance against the champions-elect.
Strutting around the Stamford Bridge turf like he owned the place, the win over Liverpool seemed like a watershed moment. Surely it’s only onwards and upwards from here.
But how will he react if he’s on the bench against Everton on Sunday? Those involved with Gilmour on a day-to-day basis at the club’s Cobham HQ believe he has got the temperament to handle it.
Evidently, so does Liverpool left-back and Scotland captain Andy Robertson.
He is now on the cusp of breaking into the national team given his impressive form at Chelsea
‘I was actually speaking to Andy,’ said Gilmour. ‘He told me: “Keep doing what you’re doing. You’re doing really well and well done’.’
Scotland manager Steve Clarke was also at Stamford Bridge to watch Gilmour turn in the performance of his life on Tuesday night.
How long before Gilmour is lining up beside Robertson for the national team?