Rewind back to 2008 and Wilshere has hotly tipped to become one of England's best-ever players.
As a creative outlet with an abundance of natural talent, Wilshere was said to have "Spanish technique, with an English heart" according to Arsenal manager, Arsene Wenger.
But unfortunately for the Englishman, the promise of his youth never came to fruition, with a succession of injuries hampering his career.
Now, the 29-year-old is rumoured to be considering retirement after failing to force his way back into Bournemouth's plans.
A sad and premature ending for a player once viewed with so much potential. However, even in his limited number of appearances, Wilshere managed to create an abundance of iconic moments.
An early Gunner
Born in Stevenage, Wilshere was first picked up by Arsenal in 2001, where he started climbing through the ranks.
After starring in Arsenal's academy for seven years, which included scoring a hat-trick for the under-18s under the watchful eye of Wenger, Wilshere was promoted to the first team in 2008 where he was handed the No. 19 shirt.
It didn't take long for Wenger to give Wilshere his chance, and he came on for his debut as a substitute against Blackburn Rovers.
To this day, Wilshere is Arsenal's youngest ever league debutant at 16 years and 256 days.
Clearly boosted by his debut, Wilshere took just ten days more to net his first goal in an Arsenal shirt, notching in a 6-0 drubbing of Sheffield United in the League Cup.
In November of the same year, Wilshere also came on in the Champions League against Dynamo Kyiv to make him just the fifth 16-year-old to appear in the competition.
During the Christmas period, Wilshere was loaned out to Bolton Wanderers, but Wenger was clearly keen to integrate him into the Arsenal side, and refused their bids for a permanent transfer over the summer.
Just a year into his Gunners career, Wilshere had nailed down a spot in the first-team squad.
A masterclass against Barcelona
Following his loan spell at Bolton, Wilshere became an established member of the Gunners side in 2010/11, going on to make 35 Premier League appearances for the north London side.
Arsenal finished fourth and Wilshere only managed a single goal in the league campaign, but it was in Europe where he truly announced himself.
The Gunners managed second place in their Champions League group, which contained Serbian side Partizan, Braga and eventual group winners Shakhtar Donetsk.
Wenger's side entered the tie as clear underdogs against a side that featured Lionel Messi, Xavi and Andres Iniesta.
But in the first leg of the tie at the Emirates Stadium, it was Wilshere who stole the headlines ahead of the legendary Spanish trio.
At just 19 years of age, Wilshere produced a masterful performance as he went toe-to-toe with some of the best midfielders the game has ever seen.
Barcelona opened the scoring via David Villa, but late goals from Van Persie and Andrei Arshavin secured a first-leg advantage for Arsenal.
Following the game, praise flooded in for the teenage sensation, including from opposition manager Guardiola who called Wilshere "a top player", as well as Xavi who admitted the Englishman "played a fantastic game".
FA Cup success
Despite never winning the Premier League with Arsenal, Wilshere did play a part in their consecutive FA Cup wins in 2014 and 2015.
After last winning the cup in 2005, Arsenal went all the way in 2014, although they almost tripped at the final hurdle against the most unlikely of opposition.
The Gunners saw off Wigan Athletic in the semi-finals after a tense penalty shootout at Wembley, which set up a finale against Hull City.
Wenger's side entered as strong favourites, but they certainly didn't live up to their billing in the first half as the Tigers took a 2-0 lead within 10 minutes courtesy of James Chester and Curtis Davies.
Wilshere was limited to a spot on the bench for the final, but after goals from Santi Cazorla and Laurent Koscielny took the game to extra time, Wenger called on his midfield maestro for the final 15 minutes.
Just four minutes after Wilshere's introduction, Arsenal completed their remarkable comeback thanks to an Aaron Ramsey goal, which proved to be the winner.
A record-levelling 11th win in the competition for the Gunners drew them level with Manchester United for FA Cup wins, but they weren't done yet.
The next year, they managed to again reach the final thanks to Alexis Sanchez' extra-time goal against Reading.
Aston Villa awaited them, but the Villains were blown away in the final, with four second-half goals from Arsenal completing a 4-0 win.
Wilshere was again named as a substitute, but made an appearance in the second half after replacing Mesut Ozil with 13 minutes to play.
Time with the Three Lions
After his emergence at Arsenal, Wilshere didn't take long to catch the eye of Fabio Capello and the England set-up.
Wilshere featured for the under-21 side in 2009 before being called up to the senior team just a year later.
Four days after his call-up, Wilshere came on to replace Steven Gerrard in a friendly against Hungary. At the age of 18 years and 222 days, he was the 10th youngest player to represent the Three Lions.
In 2012, Wilshere played a major part in England's Euro qualifying games, but unfortunately missed the tournament itself after suffering an injury - a common theme in his career.
Under Roy Hodgson, WIlshere continued to be a part of the England side, and was named as part of the 2014 World Cup squad. However, his only minutes came in the final group game against Costa Rica, when England had already been eliminated.
Wilshere was also called up for England's torrid Euro 2016 campaign after impressing in the qualifiers. He was reportedly still suffering with an injury, however, and only started in the 0-0 draw against Slovakia before coming on in the 2-1 defeat to Iceland.
On loan to his boyhood club
As Wilshere continued to struggle for consistent game-time, he decided to try and reignite his career out on loan at West Ham - the club he supported as a child.
He made his debut in a 4-0 loss to Liverpool and that pretty much set the tone for the rest of his loan spell. He managed just 19 appearances for the Hammers across two seasons before his contract was mutually terminated in October 2020.
Still with the belief he could play at the top level, Wilshere signed with Bournemouth in January 2021. However, it turned out to be the same old story for the midfielder and he made just 14 appearances for the Cherries before he was released at the end of the season.