There was a time when Liverpool would have regretted letting Dele Alli slip through their fingers.
There was a time when the Reds would have been battling with clubs all over the continent for the England international’s signature, had there been any suggestion that he was set to leave Tottenham Hotspur.
There was a time when the former MK Dons starlet would have been suggested as a potential replacement for a Philippe Coutinho or Gini Wijnaldum if Jurgen Klopp was in need of bolstering his midfield ranks.
But those days have long since passed, with the midfielder’s decline since helping England reach the 2018 World Cup semi-finals belatedly prompting Spurs to push Dele towards the exit door.
Remaining out of favour under new boss Antonio Conte, Sky Sports News are reporting that Tottenham will listen to formal offers for the 25-year-old in January with his future unclear as a result.
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It’s a stark contrast to the position he found himself in when bursting onto the scene as a teenager with MK Dons, making his debut as a 16-year-old in November 2012 before earning a £5m move to Spurs less than three years later after shining in League One.
A boyhood Liverpool fan who grew up idolising Steven Gerrard, the Reds were also in for his signature prior to his move to Spurs, and had looked favourites to sign him at one point as a result due to his allegiances.
He even met manager Brendan Rodgers in a hotel for talks, with the Northern Irishman convinced Liverpool had got their man, only for a move to never materialise for a variety of reasons.
“We thought we had him at Liverpool,” Rodgers admitted in 2016. “The manager of MK Dons actually drove him down to us. They played a game on the Saturday and we were playing West Ham on the Sunday.
“We’d had contact with Dele, it was all above board, I was speaking with Karl Robinson and I spoke to Dele and his adoptive parents.
“Karl did really well with him and he came to me and said: ‘I’ve got a really exciting player, I’d love to see him at Liverpool’.
“I spent a couple of hours in a hotel room with him and he wanted to come to Liverpool. It was all about getting the deal done with the club but unfortunately it never got done.
“On Saturday evening we thought it had got done but eventually he went to Tottenham, which was frustrating and disappointing. He’s done really well there.”
With Robinson a Liverpool fan and former Reds coach, his old club had been aware of Dele for some time with Rodgers pictured scouting the midfielder as early as January 2014 as MK Dons drew 3-3 with Wigan Athletic.
“I know Brendan quite well and we speak about different players all the time,” Robinson would confirm after that particular match. “I don't know the reason why he was at the game but Dele is special.
“You will have seen him do some silly things because he is 17 years of age but he produced some bits of magic and you don't see many of them playing in an FA Cup third-round tie against a very good Wigan side and not look out of place.”
Liverpool’s efforts to sign Dele also saw them promise him he could meet his boyhood hero, Gerrard, only for the Reds skipper to miss the meeting.
“At the time when I was at MK there was contact with Liverpool before I signed for Tottenham, but that was before we’d even spoke to Tottenham,” Dele told Football Focus in 2016. “I think it was six months before.
“We went up there and I think they knew that Steven Gerrard was my hero, so they said he was going to come down to meet me, but when I got there he was asleep apparently.
“I think he had a game the next day though so I understand.”
Not that that stopped Dele from idolising the Reds legend.
“Steven Gerrard was someone I looked up to massively,” he would admit to FourFourTwo. “I'd always try to copy him, right down to the boots he was wearing.
“It was his attitude on the pitch that stood out - you could really see how much he hated losing.
"The moment that stands out is the goal against West Ham in the FA Cup final. It was a great moment in a huge game, and a great finish too. It's one of the first goals I remember seeing.
"I had a picture with him when I was younger, but I've never spoken to him. I think he'd probably be the only person that would make me a bit star-struck!"
Dele was inevitably suggested as a long-term replacement for Gerrard as a result when linked with Liverpool, yet the move fell through with then CEO Ian Ayre later claiming that the club felt he wasn’t worth the fee MK Dons were demanding.
"There was interest in the player, but where it got to was that the demands at that time were not fitting to what he had achieved at that point," Ayre said at a lecture in Liverpool five years ago.
"We didn't feel the player matched that demand. It's easy to sit and say: 'Look what you could have bought,' but how many players could you apply the reverse of that to? That's the truth."
Signing for Spurs in February 2015, Dele finished that season back on loan with MK Dons as he scored 16 goals in 39 League One appearances to help the club win promotion to the Championship, with his displays seeing him named Football League Young Player of the Year and earn a place in the League One PFA Team of the Year.
But as his former team-mates struggled in the second tier without him, suffering relegation straight back to League One, he wasted no time in shining in the English top-flight.
He scored 10 goals from 33 Premier League appearances in his first season with Spurs, including a spectacular Goal of the Season winner against Crystal Palace, as he helped the North London outfit qualify for the Champions League.
It was some maiden year in the Premier League as Liverpool were left to rue letting Dele slip through their fingers, with Gerrard, by now at LA Galaxy, publicly cursing the Reds’ failure to sign the midfielder.
“I was actually disappointed Liverpool didn’t sign him,” he would tell BT Sport. “I thought he was certainly a player Liverpool might have tried to go for, especially with me coming toward the end.
“He’s a player I could see playing for Liverpool for 10-15 years, he’s certainly got that ability.
“I hope (he's the next Steven Gerrard), that’s very flattering for me. For me he looks to be a little more ahead of me as far as England’s games and appearances are concerned.
“He’s got more experience because he came through at MK Dons, that helped him progress and make the impact that he has done at Tottenham.”
And while Liverpool might have been left to curse not signing Dele, he had no regrets about his decision to sign for Tottenham.
"I have always had confidence in my ability, I knew I'd get a chance coming here, that's one of the main reasons why I signed for Tottenham,” he said in April 2016. "We've got a great manager who does work a lot with youngsters.
"You can see that this season. We've got great youngsters in the team and everyone is looking to fight for their place."
Dele’s form in his maiden season with Spurs saw him named PFA Young Player of the Year, earn a place in the Premier League PFA Team of the Year and handed a maiden international call-up, England debut and place in the Three Lions’ squad for Euro 2016.
Yet more was to come in 2016/17 as he enjoyed the best season of his career to date, scoring 22 goals from 50 appearances in all competitions (18 goals from 37 in league appearances) as Spurs clinched their best ever Premier League standing by finishing second in the table.
His individual displays unsurprisingly saw Dele again named PFA Young Player of the Year and earn a place in the Premier League PFA Team of the Year, but he was unable to replicate such heights in 2017/18.
Spurs would still qualify for the Champions League by finishing third, as well as reach the FA Cup semi-finals, while he would score 14 goals in all competitions to secure his place in England’s squad for the 2018 World Cup.
And while he would finish the 2018/19 season in a Champions League final, what should have been the highlight of his career and platform to build from has instead been his stage to fall from, with injuries ensuring a loss of form was just around the corner and preventing him from repeating his mesmerising early Tottenham displays.
Limited to 25 Premier League appearances in both 2018/19 and 2019/20, he started Tottenham's Champions League final loss to Liverpool, only to be replaced late on against his boyhood side and was unable to hide his frustrations as Spurs went on to suffer a 2-0 defeat.
Perhaps, if Gerrard had not been napping or if the Reds had had more funds to play with, Dele would have instead been celebrating in Red alongside the likes of Jordan Henderson in Madrid.
Instead, his career was about to nose-dive.
Manager Mauricio Pochettino was sacked in November 2019 and the midfielder quickly fell out of favour under his replacement, Jose Mourinho, as his loss of form continued. Only this time injuries were not to blame.
Making just 15 Premier League appearances under the Portuguese last season, the appointments of first Nuno Espirito Santo and now Conte have failed to arrest his decline, prompting him to now be made available for transfer.
Still only 25, there is still plenty of time for Dele to rediscover his past heights and get back to his best, but it looks like it won’t be at the Tottenham Hotspur Stadium.
Yet Liverpool will have no desire to make up for their apparent mistake of 2015, such has been his decline, even if he is made available at a cut-price fee.
At one stage a suitable contender to be the ‘next Steven Gerrard’, he has failed to live up to that tag and it would take some revival for the England international to force his way back onto the Reds’ transfer radar.
But as Dele considers his next move following Tottenham’s decision to transfer-list him, he’ll be desperate to recapture his past form and again make Liverpool rue missing out on signing him wherever he ends up next.
