Dominic Solanke will be hoping he can make it third time lucky.
After two previous spells at clubs in English football's 'big six', Solanke's move to Spurs from Bournemouth, which could be worth up to £65m, provides him with another chance to prove he belongs on the biggest stage.
He was unable to make the breakthrough he wanted as a youngster at Chelsea and Liverpool, but last season's prolific campaign with the Cherries established the 26-year-old as one of the country's leading forwards.
BBC Sport's Nizaar Kinsella said: "Bournemouth didn't want to sell but will feel the bid of £55m plus £10m add-ons they accepted represents the value of Solanke's £65m release clause.
"They initially didn't expect anyone to hit that number, but some flexibility was shown on payment terms given Solanke was pushing to leave to play European football and try to earn a future place with England."
There are mixed views about Solanke's price tag, especially considering last season's 19 goals was the first time he has scored more than 10 in a Premier League campaign.
So is Solanke value for money for Tottenham? And where does he fit among their attacking options?
Solanke will be playing in the Europa League with Spurs in the coming season and hoping a move to one of the Premier League's 'big six' will help him add to his solitary England cap.
And a look at last season's headline stats suggests he has more than earned another crack at the big time.
He finished the campaign as the Premier League's fourth top scorer with 19 goals, five more than anyone else playing for a bottom-half team.
But there must have been a time when Solanke thought another opportunity like this would not come again.
The Chelsea academy product was prolific at youth level for the Blues and played a key role in England Under-20s' World Cup win in 2017, finishing joint-top scorer with four goals.
However, his sole Chelsea appearance came as a substitute in a Champions League win against NK Maribor in 2014, and he moved to Liverpool for about £3m at the end of his contract in 2017.
The striker earned his only England cap as a 75th-minute substitute against Brazil in November 2017, but struggled to establish himself at Liverpool.
He made 21 appearances in his first season at Anfield, 16 of them from the bench, scoring just once - and did not play for the Reds the following campaign before joining Bournemouth for £19m in January 2019.
Questions about his goalscoring abilities remained - he netted just three times in his first 42 Premier League appearances for Bournemouth.
And after an impressive 29 goals to help the Cherries up from the Championship, he again struggled to recreate his output in the top flight, with just six Premier League goals in 2022-23 - including a goal drought of more than 17 hours.
However, just when Solanke was in danger of being written off, he enjoyed a season to remember.
When Harry Kane left Tottenham last summer for Bayern Munich, manager Ange Postecoglou did not sign a striker to replace the club's all-time leading scorer.
But with Spurs having finished with just 74 goals last campaign - the least in the top seven - it is no surprise to see them try to boost their firepower.
Kinsella said: "The signing of a new striker was never supposed to spark the exit of Brazil striker Richarlison, with Postecoglou confirming his faith in him.
"He believes they needed another option as they missed Richarlison when he was injured, with no natural alternative.
"Postecoglou believes Solanke will be the perfect fit for his system. That is down to his running ability, pressing skills and goal output.
"He isn't going to pin all his hopes on Solanke scoring goals though, as his style of play should mean players from all over the pitch will chip in."
So what do the stats say?
Solanke was only the 10th player in Premier League history to score as many as 19 goals for a bottom-half team - with no player's goals worth more points to their club than his last season, according to data analysts Opta.
He compares well in other areas as well, ranking fourth in the Premier League for expected goals (xG) in 2023-24 (19.6), third for shots (109) and sixth for touches in the opposition box (239).
Son Heung-min ranked best for Tottenham last season with 85 shots, 12.09 xG and 227 touches in the opposition box.
Solanke's numbers also suggest he is a good fit for Tottenham's intense pressing game, with Spurs one of the few teams who pressed more than Bournemouth last campaign.
Opta say Solanke led the Premier League last season for pressures (1,242), pressures in the final third (703) and pressures in the final third resulting in a turnover (142).
Bournemouth boss Andoni Iraola has admitted the Cherries will struggle to replace Solanke, saying: "Dominic deserved to be called up for the Euros and to not be was a blow for him. He has given us everything he has but to sign someone like Dom is almost impossible."
Despite his stunning campaign last time round, there will still be questions about Solanke's value.
His 19 goals last season were actually an underperformance compared to his non-penalty xG by 0.6 - and he scored just six goals in his only other full Premier League season for Bournemouth.
Football Transfers, external, a platform which uses player data algorithms to derive Estimated Player Values (ETV), believes Solanke is worth £33.1m, but suggests there are a number of reasons why he has been sold for more than that.
Being an English player in a deal involving two clubs is one factor, as has the dearth of alternative striking options.
Brentford's Ivan Toney has only scored four league goals since his return from an eight-month betting ban and is two years older than Solanke, while Everton's Dominic Calvert-Lewin, 27, has struggled for form and fitness in recent seasons.
Football Transfers' Paul MacDonald said: "All in all, Solanke is overvalued for a player who hasn't played Champions League, isn't an international regular, and isn't particularly young any more.
"But he's one of the best players in that position who is available and he's got a decent strike rate over a few seasons compared to his peers."