Kane pertama bermain untuk klub lokal Ridgeway Rovers, dan bergabung dengan akademi muda [[Arsenal F.C.|Arsenal]] ketika ia masih berumur 8 tahun. Ia dilepas setelah satu musim; manager [[Arsène Wenger]] menyatakan pada November 2015 bahwa ia kecewa [[Arsenal F.C.|Arsenal]] memilih untuk melepas Kane.<ref>{{cite news|last=Hytner|first=David|title=Arsène Wenger: I was angry when I found out Arsenal had let Harry Kane go|url=https://www.theguardian.com/football/2015/nov/06/arsene-wenger-arsenal-tottenham-harry-kane|accessdate=8 November 2015|newspaper=The Guardian|location=London|date=6 November 2015|archive-date=2019-03-30|archive-url=https://web.archive.org/web/20190330142123/https://www.theguardian.com/football/2015/nov/06/arsene-wenger-arsenal-tottenham-harry-kane|dead-url=no}}</ref> Ia juga menjalani trial di [[Tottenham Hotspur F.C.|Tottenham Hotspur]] tapi tidak berhasil.<ref name="worrall">{{cite book |url=https://books.google.com/books?id=VH2pDgAAQBAJ&pg=PT9&lpg=PT9#v=onepage&q&f=false |title=Harry Kane – The Biography|first= Frank |last= Worrall |isbn=9781786065384 |chapter= Chapter 1: Beginnings |publisher=John Blake Publishing Ltd |date=18 MayMei 2017 }}</ref> Ia kembali ke klub lamanya, dan pada 2004, ia bergabung dengan akademik [[Watford F.C.|Watford]] untuk trial 4-6 minggu sebelum ia diberi kesempatan sekali lagi di Tottenham ketika berumur 11 tahun.<ref>{{cite news|title=Record-breaking Kane proves that Watford's loss was Tottenham's emphatic gain|url=http://www.telegraph.co.uk/sport/football/teams/tottenham-hotspur/12070870/Record-breaking-Kane-proves-that-Watfords-loss-was-Tottenhams-emphatic-gain.html|work=The Daily Telegraph|first=Gerry|last=Cox|date=27 DecemberDesember 2015|access-date=2017-10-09|archive-date=2023-05-22|archive-url=https://web.archive.org/web/20230522214539/https://www.telegraph.co.uk/sport/football/teams/tottenham-hotspur/12070870/Record-breaking-Kane-proves-that-Watfords-loss-was-Tottenhams-emphatic-gain.html|dead-url=no}}</ref> Ia pertama bermain di Tottenham sebagai [[midfieldergelandang]] – awalnya di posisi bertahan, lalu sebagai midfildergelandang menyerangserang.<ref name="worrall"/> Pada awalnya di klub, ia tidak menonjol sebagai pemain sebagaimana ia tidak besar maupun cepat, namun yang bekerja dengannya mencatat keinginannya yang konstan untuk berkembang dalam berbagai aspek permainan.<ref name="white"/> Pada [[2008–09 Tottenham Hotspur F.C. season|musim 2008–09]], ia bermain di underU-16s16 yang berkompetisi untuk turnamen Copa Chivas di [[Meksiko]], dan turnamen Bellinzona di [[Swiss]], mencetak 3 gol.<ref>{{cite web|title=Unearth themselves a striking gem|url=http://www.footballfancast.com/football-blogs/harry-kane-tottenham-unearth-themselves-a-striking-gem|publisher=Footballfancast|accessdate=21 MarchMaret 2015|archive-date=2015-04-21|archive-url=https://web.archive.org/web/20150421143020/http://www.footballfancast.com/football-blogs/harry-kane-tottenham-unearth-themselves-a-striking-gem|dead-url=no}}</ref> Pada Juli 2009, menjelang usia 16, ia menandatangani kontrak beasiswa dengan Tottenham.<ref>{{cite news |first=Sam |last=Cunningham |title=Harry Kane is a modern day journeyman who has already played for six clubs... but the Tottenham striker could be set to become Manchester United's next star |url=http://www.dailymail.co.uk/sport/football/article-3083113/Harry-Kane-modern-day-journeyman-played-six-clubs-Tottenham-striker-set-Manchester-United-s-star.html |newspaper=Daily Mail |location=London |date=15 May 2015 |accessdate=31 MarchMaret 2016 |archive-date=2016-01-24 |archive-url=https://web.archive.org/web/20160124063422/http://www.dailymail.co.uk/sport/football/article-3083113/Harry-Kane-modern-day-journeyman-played-six-clubs-Tottenham-striker-set-Manchester-United-s-star.html |dead-url=no }}{{Unreliable source?|date=April 2017}}</ref>
Pada [[2009–10 Tottenham Hotspur F.C. season|musim 2009–10]], Kane bermain 22 kali untuk Tottenham U-18, dan mencetak 18 gol.<ref>{{cite web |url=http://www.footballfancast.com/2010/09/football-blogs/harry-kane-tottenham-unearth-themselves-a-striking-gem |title=Tottenham unearth themselves a striking gem |date=10 September 2010 |publisher=FootballFanCast.com |access-date=2017-10-09 |archive-date=2013-12-03 |archive-url=https://web.archive.org/web/20131203004154/http://www.footballfancast.com/2010/09/football-blogs/harry-kane-tottenham-unearth-themselves-a-striking-gem |dead-url=yes }}</ref> Ia menandatangani kontrak profesional pertamanya pada Juli 2010.<ref>{{cite news |title=Kane in O's loan |url=http://www.tottenhamhotspur.com/news/kane-in-os-loan-070111/ |publisher=Tottenham Hotspur F.C. |date=7 JanuaryJanuari 2011 |accessdate=31 MarchMaret 2016 |archive-date=2018-07-01 |archive-url=https://web.archive.org/web/20180701170504/http://www.tottenhamhotspur.com/news/kane-in-os-loan-070111/ |dead-url=no }}</ref> Kane muncul di bangku cadangan tim utama 2 kali ketika musim 2009–10.<ref>{{cite web |title=Results/matches: 2009/10 |url=http://www.soccerbase.com/teams/team.sd?team_id=2590&teamTabs=results&season_id=139 |work=Soccerbase |publisher=Centurycomm |accessdate=31 MarchMaret 2016 |archive-date=2018-07-04 |archive-url=https://web.archive.org/web/20180704213811/http://www.soccerbase.com/teams/team.sd?team_id=2590&teamTabs=results&season_id=139 |dead-url=no }}</ref> Keduanya merupakan kemenangan tuan rumah kompetisi domestik: satu merupakan laga [[EFL Cup|League Cup]] melawan [[Everton F.C.|Everton]] pada 27 Oktober 2009<ref>{{cite news|title=Tottenham 2–0 Everton|url=http://news.bbc.co.uk/sport1/hi/football/league_cup/8323083.stm|accessdate=11 JanuaryJanuari 2015|publisher=BBC Sport|date=27 OctoberOktober 2009|archive-date=2023-08-16|archive-url=https://web.archive.org/web/20230816175622/http://news.bbc.co.uk/sport2/hi/football/league_cup/8323083.stm|dead-url=no}}</ref> dan satunya adalah ulangan ronde keempat [[FAPiala CupFA]] melawan [[Bolton Wanderers F.C.|Bolton Wanderers]] pada 24 Februari 2010.<ref>{{cite news|last=Roopanarine|first=Les|title=Tottenham 4–0 Bolton|url=http://news.bbc.co.uk/sport1/hi/football/fa_cup/8528819.stm|accessdate=11 JanuaryJanuari 2015|publisher=BBC Sport|date=24 FebruaryFebruari 2010|archive-date=2021-12-08|archive-url=https://web.archive.org/web/20211208163825/http://news.bbc.co.uk/sport1/hi/football/fa_cup/8528819.stm|dead-url=no}}</ref>
==== Musim 2010-11 ====
Pada 7 Januari 2011, Kane pindah ke [[Leyton Orient F.C.|Leyton Orient]] sebagai [[Loan (sports)|pinjaman]] hingga [[2010–11 Leyton Orient F.C. season|musim 2010–11]] berakhir.<ref>{{cite news |url=http://news.bbc.co.uk/sport1/hi/football/teams/l/leyton_orient/9349908.stm |title=Leyton Orient sign Harry Kane & Andrew Whing |date=7 JanuaryJanuari 2011 |publisher=BBC Sport |access-date=2017-10-09 |archive-date=2020-06-20 |archive-url=https://web.archive.org/web/20200620134144/http://news.bbc.co.uk/sport1/hi/football/teams/l/leyton_orient/9349908.stm |dead-url=no }}</ref> Manajer [[Russell Slade]] "senang" dengan kedatangan Kane dan mengatakan, "Saya yakin ia akan berperan penting dalam beberapa bulan ke depan".<ref name="Harry">{{cite web|title=From Leyton Orient to Tottenham's first team via Millwall: Charting the rise of Harry Kane|url=http://www.skysports.com/football/news/11660/9734189/from-leyton-orient-to-tottenhams-first-team-via-millwall-charting-the-rise-of-harry-kane|publisher=Sky Sports|accessdate=18 AugustAgustus 2015|archive-date=2019-12-20|archive-url=https://web.archive.org/web/20191220171834/https://www.skysports.com/football/news/11660/9734189/from-leyton-orient-to-tottenhams-first-team-via-millwall-charting-the-rise-of-harry-kane|dead-url=no}}</ref> Ia memulai debut tim utama untuk Orient pada 15 Januari, sebagai [[Substitutepemain (association football)|pengganti]]. Ia menggantikan [[Scott McGleish]] di menit 73 ketika seri 1–1 dimelawan [[Rochdale A.F.C.|Rochdale]].<ref>{{cite news|url=http://news.bbc.co.uk/sport1/hi/football/eng_div_2/9359393.stm#blq-nav |title=Rochdale 1–1 Leyton Orient |date=15 JanuaryJanuari 2011 |publisher=BBC Sport}}</ref> Seminggu kemudian, Kane mencetak gol tim utama pertama melawan [[Sheffield Wednesday F.C.|Sheffield Wednesday]]; pertama kali sebagai starter, Kane yang "tidak dijaga" mencetak dari freekick [[Dean Cox (English footballer)|Dean Cox]] di menit 57 yang mana Orient menang 4–0.<ref>{{cite news |url=http://news.bbc.co.uk/sport1/hi/football/eng_div_2/9362036.stm |title=Leyton Orient 4–0 Sheffield Wednesday |date=22 JanuaryJanuari 2011 |publisher=BBC Sport |access-date=2017-10-09 |archive-date=2021-12-22 |archive-url=https://web.archive.org/web/20211222075156/http://news.bbc.co.uk/sport1/hi/football/eng_div_2/9362036.stm |dead-url=no }}</ref><ref>{{cite web|title=Four-star Orient stun Owls|url=http://www.skysports.com/football/leyton-or-vs-sheff-wed/report/216323|publisher=Sky Sports|accessdate=18 August 2015|archive-date=2019-12-20|archive-url=https://web.archive.org/web/20191220173343/https://www.skysports.com/football/leyton-or-vs-sheff-wed/report/216323|dead-url=no}}</ref> Slade mengatakan ia "senang" Kane mencetak gol pertama sebagai starter pertama kali.<ref name="Harry"/> Pada 12 Februari, ia mencetak 2 gol dalam kemenangan 4–1 atas [[Bristol Rovers F.C.|Bristol Rovers]], menjadi pengganti McGleish di menit 70.<ref>{{cite news|url=http://news.bbc.co.uk/sport1/hi/football/eng_div_2/9387845.stm |title=Leyton Orient 4–1 Bristol Rovers |date=12 FebruaryFebruari 2011 |publisher=BBC Sport}}</ref> Ia mengakhiri musim mencetak 5 gol dari 18 pertandingan.<ref name="Kane">{{cite news|title=Harry Kane timeline: How has the Spurs starlet gone from peripheral figure to England goalscorer?|url=http://www.mirror.co.uk/sport/football/news/harry-kane-timeline-how-spurs-5405662|newspaper=Daily Mirror|location=London|accessdate=18 AugustAgustus 2015|archive-date=2015-06-30|archive-url=https://web.archive.org/web/20150630035612/http://www.mirror.co.uk/sport/football/news/harry-kane-timeline-how-spurs-5405662|dead-url=no}}</ref>
