Now sitting atop the British tennis charts, Jack Draper will hope that the third time is the charm as far as an ATP Tour title is concerned, as he battles Matteo Berrettini in Sunday's Stuttgart Open final.
The sixth seed followed up his beating of defending champion Frances Tiafoe with a straight-sets semi-final success over Brandon Nakashima, while his Italian foe conquered compatriot Lorenzo Musetti on Saturday.
Match preview
Whether Draper finally clinches his maiden ATP Tour crown or is left to lament a third straight defeat in showpiece matches, the 22-year-old will end his maiden grass-court tournament of the season safe in the knowledge that he is Great Britain's current best men's tennis player.
Recovering expertly from his shock first-round French Open exit to Dutch qualifier Jesper de Jong, Draper sunk Sebastian Ofner and Marcos Giron - who denied him an all-British clash with Andy Murray - in his opening two BOSS Open battles before fighting back to send reigning champion Tiafoe packing.
Draper's defeat of the holder saw another British-American affair materialise between the 22-year-old and Brandon Nakashima, former foes in the 2022 Next Gen ATP Finals - which Nakashima won - but the ace-happy Draper avenged that beatdown with a 6-3 6-3 triumph in one hour and 12 minutes.
Producing a masterclass in serving all week, the 22-year-old fired another 13 aces and did not face a single break point over the course of Saturday's semi-final, thereby ensuring a rise to 35th in the world and overtaking Cameron Norrie to become the new British men's number one.
Not since Murray himself in November 2009 has there been a younger man atop the British singles rankings, but Draper has already been forced to accept two runners-up prizes in top-level finals, losing last year's Sofia Open to Adrian Mannarino and January's Adelaide showpiece to Jiri Lehecka.
As well as his serving mastery on the grass, Draper still possesses the best break-point conversion rate on the ATP Tour in the last 52 weeks (48.4%), but standing in his way of a slice of stardom is a man who knows better than most how to triumph on the Stuttgart soil.
A two-time champion of the BOSS Open in 2019 and 2022 - conquering Murray in the latter final - Italian Grand Slam finalist Berrettini is hitting new zeniths on his comeback trail, having been riddled by injuries over the past 12 months, missing both majors this year as a result.
However, the 28-year-old clinched his eighth ATP Tour crown in Morocco two months ago and has come out on the correct end of some marathon matches to return to the Stuttgart showpiece, eliminating Giovanni Mpetshi Perricard and Dominik Koepfer in thrilling circumstances before seeing Alexander Bublik retire from their quarter-final.
A tie with fifth seed Lorenzo Musetti would ostensibly prove a taxing test, but Berrettini outclassed his colleague with a near-impeccable display, committing just seven unforced errors and saving all four break points in an emphatic 6-4 6-0 success to reach his 14th top-level final.
Three years on from falling to Novak Djokovic's superiority in the 2021 Wimbledon final, Berrettini - who is also a US Open and Australian Open semi-finalist - is making waves on the grass once more, and victory for either competitor on Sunday should be met with smiles by the neutrals.
Tournament so far
Jack Draper:
First round: vs. Sebastian Ofner 7-6[4] 7-6[5]
Second round: vs. Marcos Giron 6-4 3-6 6-3
Quarter-final: vs. Frances Tiafoe 5-7 6-4 7-6[1]
Semi-final: vs. Brandon Nakashima 6-3 6-3
Matteo Berrettini:
First round: vs. Giovanni Mpetshi Perricard 7-6[9] 7-6[9]
Second round: vs. Dominik Koepfer 6-7[9] 7-6[5] 6-3
Quarter-final: vs. Alexander Bublik 4-6 6-1 1-0 ret.
Semi-final: vs. Lorenzo Musetti 6-4 6-0
Head To Head
Sunday's Stuttgart trophy match will mark the maiden ATP Tour singles meeting between Draper and Berrettini, the former of whom plays with a tricky left-handed style, while his Italian foe is a more orthodox right-hander.
Both men possess intimidating physical frames, but the 6ft 4in Draper will not be the tallest man on the court this Sunday, as Berrettini comes in marginally taller at 6ft 5in.
While Draper has a 0% success rate in ATP Tour finals owing to his pair of losses, Berrettini has eight titles to show from 13 showpiece contests, including four from five on grass, the outlier being Wimbledon 2021.
We say: Berrettini to win in three sets
Expect a flurry of aces to fly into the back walls during Sunday's final between two titanic servers - Draper fired an astounding 31 in his beating of Tiafoe - and the 22-year-old is finally showing what he is truly capable on the grass now that he has consigned his injury woes to the past.
Berrettini can empathise in that regard, but the Italian is a seasoned grass-court champion and arguably mixes up his approach to better effect than his British foe, whose wait for a top-level crown should continue as the 28-year-old conquers Stuttgart for the third time.
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