Now he's preparing to mark Cristiano Ronaldo in next week's Champions League final and is the emblematic figure of a youthful and boldly assembled England squad heading to the World Cup in Russian Federation.
Sterling is vastly improved under Manchester City boss Pep Guardiola and one of the few current England players who can be described as world class, while Alli has the potential to hit the same heights. The 22-year-old's form across a season-long loan with Crystal Palace earned him the nod over Arsenal's Wilshere and Newcastle United'sJonjo Shelvey, both of whom had their champions. "They're both good guys and have contributed a lot throughout qualification, so it wasn't an enjoyable part of the job and I feel it's important to acknowledge their contribution in getting us to Russian Federation".
Three members of the Premier League-winning Manchester City defence - Fabian Delph, John Stones and Kyle Walker - have been selected along with Liverpool youngster Trent Alexander-Arnold.
"I would say this is an experience, take total pressure off them, say, "It is all about experience, we are not going to do particularly well, we are not going to win this World Cup".
Speaking to talkSPORT host Jim White, Lineker said: "When you look at the squad there are some brilliant young players there and with a little bit of patience and a little bit of nurture, they could be superstars".
But the most striking inclusion is uncapped teenager Alexander-Arnold.
I don't think we've got any really good midfield passers of the ball for Jack not to be in it, quite frankly.
'This is a squad which we can be excited about, ' said Southgate.
"I found out this morning, just before we came out to Marbella", he told the club's official website. "When we pick young players, it's not just because they are young, it's because their performances deserve it".
"Mum we're off to the World Cup!".
"But at the next World Cup, given the success England have had at youth levels which we've never had before, it bodes really well".
England have warm-up friendlies against Nigeria at Wembley on June 2 and Costa Rica in Leeds on June 7, with the Group G opener against Tunisia on June 18.