While 2023 marked the beginning of what could be the 'Ange Postecoglou era' at Tottenham Hotspur, it also coincided with the end of Harry Kane's stellar spell in north London, with the academy graduate finally moving on after over a decade in the first team.
The 30-year-old is currently staring down the barrel of a trophyless first season at Bayern Munich, although with 24 Bundesliga goals to his name already in 2023/24, it is easy to recognise just how far he has come since arriving on the scene with the Lilywhites.
For all Tottenham's record scorer has gone on to achieve in the game, such individual success did not always look to be on the cards, however, particularly amid a difficult start to life in senior football amid a handful of loan spells across the English football pyramid.
It wasn't until the 2014/15 season that Kane – who scored 21 Premier League goals that year – truly announced himself to the wider world, with his Spurs debut having actually come a few years prior at home to Hearts in a Europa League Qualifying Play-offs round second leg tie.
That goalless draw with the Scottish Premiership side back in August 2011 was the striker's first taste of senior action as a mere teenager, as he lined up alongside an eclectic mix of names who have gone on to endure far less fruitful careers elsewhere…
1 GK – Carlo Cudicini
Lining up in the sticks on the night was former Chelsea man, Carlo Cudicini, with the Italian shot-stopper having arrived at the club two years earlier after almost a decade at Stamford Bridge.
After spending just three years with the Lilywhites, the veteran 'keeper swiftly retired in 2013 following a brief stint in the MLS, before joining the Republic of Ireland U21's coaching staff.
Since 2019, the 50-year-old has been working back with the Blues as one of their 'loan player technical coaches', having initially made his return as an assistant coach to Antonio Conte in west London.
Chelsea
36
12
LA Galaxy
Retired
2 RB – Ryan Fredericks
One of the few players on this list who is still plying his trade in the Premier League, Ryan Fredericks was also handed his debut for Spurs on the night alongside Kane, acquitting himself well as the home side kept a clean sheet.
Despite going on to make just two more appearances for the club prior to sealing a permanent exit in 2015, the 31-year-old has since enjoyed stints at the likes of Fulham, West Ham United and Bournemouth, albeit while having yet to feature for the latter side this season.
Academy
3
0
Bristol City
Bournemouth
3 CB – Michael Dawson
Now part of Sky Sports' Soccer Saturday panel, Michael Dawson was one of the more senior members of the side against Hearts, leading the club as captain at the centre of defence.
After spending nine years at the club following his arrival in 2005, the former England international eventually ended his playing career with Nottingham Forest in 2021, having previously risen up through the youth ranks at the City Ground.
Nottingham Forest
321
10
Hull City
Retired
4 CB – Sebastien Bassong
Lining up alongside Dawson on the night for Harry Redknapp's side was the club's £8m signing, Sebastien Bassong, with the Cameroon international having joined from Newcastle United two years earlier.
Despite previously winning the Magpies' 'Player of the Year award, the Paris native was unable to replicate those feats during his three years in north London, making just 70 appearances in all competitions in that time.
After leaving White Hart Lane, the 37-year-old spent time at the likes of Norwich City and Peterborough United, before calling time on his playing career in 2019 following a brief stint at Greek side Volos.
Newcastle United
70
3
Norwich City
Retired
5 LB – Vedran Corluka
While typically a centre-back, the Croatian ace lined up at left-back for the visit of the Jambos in what was one of just eight appearances he made that season, prior to joining Bayer Leverkusen on loan in January 2012.
A friend and international colleague of Luka Modric, the 6 foot 4 brute was "a very tenacious, uncompromising defender" – according to teammate Roman Pavlyuchenko – albeit having swiftly tumbled down the pecking order under Redknapp.
Having ended his career in 2021 after almost a decade at Lokomotiv Moscow, the 38-year-old is now assistant coach of the Croatian national team.
Manchester City
108
1
Lokomotiv Moscow
Retired
6 DM – Tom Huddlestone
The man with a cannon of a right foot, Tom Huddlestone enjoyed a respectable albeit unspectacular seven-year stint at White Hart Lane, racking up 47 goals and assists in 209 games in all competitions for the club, after signing from Derby County in 2005.
A second-half substitute during Spurs' last trophy win in the Carling Cup final back in 2008, the Englishman eventually moved on to Hull City in 2013 – prior to ending his career with the Tigers in 2022 after a stint back at Derby.
Now 37, the Nottingham native is currently on the books at Manchester United in a unique player-coach role for the U21s, having been brought in by the Red Devils to pass on his experience to the club's emerging talent.
Derby County
209
16
Hull City
Man Utd U21's
7 CM – Tom Carroll
At one stage tipped to be the 'next Luka Modric, Kane's former academy colleague wasn't quite able to establish himself with the Lilywhites, eventually falling by the wayside amid the rise of the likes of Harry Winks under Mauricio Pochettino.
Having been sent out on a string of loans during his time at N17, it wasn't until 2017 that Carroll eventually left permanently for Swansea City, prior to featuring for the likes of Queens Park Rangers and Ipswich Town.
Now 31, the 5 foot 10 playmaker now plies his trade for League One side Exeter City, albeit having provided just one assist and no goals in 30 league games this season.
Academy
53
3
Swansea City
Exeter City
8 CM – Jake Livermore
Completing the midfield triumvirate was another promising English talent, Jake Livermore, with the academy graduate even scoring in the 5-0 first-leg thrashing of the Edinburgh-based side.
That was, however, the only goal that he would score in 58 games for Spurs in total, with much of his time at the club spent out on loan, prior to leaving permanently for Hull in 2014 – linking up with Huddlestone with the Tigers.
The 34-year-old is now on the books at Watford following a six-year spell with West Bromwich Albion, the seven-cap England international having scored three goals for the Hornets this season in the Championship.
Academy
58
1
Hull City
Watford
9 RM – Roman Pavlyuchenko
With the likes of Gareth Bale and Rafael van der Vaart afforded a rest on the night, Redknapp handed what proved to be a rare outing that season to Pavlyuchenko – the Russian striker scoring just four goals in 14 games in 2011/12.
In total, the towering forward recorded a respectable haul of 42 goals in 111 games following his arrival in 2008, albeit while only once reaching double figures for Premier League goals – scoring ten times in 2020/11.
That proved to be the marksman's only stint outside of his homeland, as he eventually hung up his boots in 2022 at the ripe old age of 40.
Spartak Moscow
111
42
Lokomotiv Moscow
Retired
10 LM – Andros Townsend
Described as the 'star turn' against Hearts by BBC Sport's Sam Lyon, Andros Townsend looked destined to make the grade at Spurs, particularly after a fruitful loan spell at QPR in 2012/13 in which he netted a stunning volley at home to Aston Villa.
Alas, the breakthrough at his parent club never truly came as the Englishman moved on to Newcastle United in 2016, before subsequent stints with Crystal Palace and Everton.
Now on the books at Luton Town, the 32-year-old has enjoyed something of a renaissance with the Hatters alongside the likes of Ross Barkley, notably scoring against former club Newcastle back in December – that diet of chicken feet seems to be working out well for the part-time talkSPORT pundit…
Academy
87
9
Newcastle United
Luton Town
