| 2008-09 | No. | Previous Club | Date | Transfer Fee | Nat | Position | Transfer To | # | ||
| X | GOMES, Heurelho | 1 | PSV Eindhoven (Netherlands) | (06-08) | £7,000,000 | BRA | Goalkeeper | 1 | 1 | |
| 2 | HUTTON Alan | 2 | Glasgow Rangers (Scotland) | (01-08) | £9,000,000 | SCO | Right Back | 2 | 2 | |
| 2 | BALE Gareth | 3 | Southampton | (05-07) | £7,500,000 | WAL | Left Back | 3 | 3 | |
| 3 | ZOKORA Didier | 4 | St. Etienne (France) | (06-06) | £5,200,000 | CIV | Midfield | 4 | 4 | |
| X | BENTLEY David | 5 | Blackburn Rovers | (07-08) | £17,000,000 | ENG | Right Winger | 5 | 5 | |
| 4 | HUDDLESTONE Tom | 6 | Derby County | (07-05) | £2,000,000 | E U21 | Midfield | 6 | 6 | |
| 4 | LENNON Aaron | 7 | Leeds United | (07-05) | £800,000 | ENG | Winger | 7 | 7 | |
| 4 | JENAS Jermaine | 8 | Newcastle United | (07-05) | £7,000,000 | ENG | Midfield | 8 | 8 | |
| X | PAVLYUCHENKO Roman | 9 | Spartak Moscow (Russia) | (08-08) | £13,800,000 | RUS | Striker | 9 | 9 | |
| 2 | BENT Darren | 10 | Charlton Athletic | (06-07) | £16,500,000 | ENG | Striker | 10 | 10 | |
| 2 | GILBERTO de Silva Melo | 11 | Hertha Berlin (Germany) | (01-08) | £1,800,000 | BRA | Left Back | 11 | 11 | |
| X | PALACIOS Wilson | 12 | Wigan Athletic | (01-09) | £12,000,000 | HON | Defensive Mid | 12 | 12 | |
| 4 | STALTERI Paul | 13 | Werder Bremen (Germany) | (07-05) | £0 | CAN | Defender | Borussia Moechengladbach | 13 | 13 |
| X | MODRIC Luka | 14 | Dinamo Zagreb (Croatia) | (04-08) | £16,505,000 | CRO | Midfield | 14 | 14 | |
| 7 | KEANE Robbie | 15 | Liverpool | (01-09) | £12,000,000 | IRL | Striker | 15 | 15 | |
| 3 | GHALY Hossam | 15 | Feyenoord (Netherlands) | (01-06) | £750,000 | EGY | Midfield | Al Nasr (Saudi Arabia) | 16 | 16 |
| 2 | GUNTER Chris | 16 | Cardiff City | (01-08) | £2,000,000 | WAL | Full Back | Loan to Nottingham Forest | 17 | 17 |
| X | DOS SANTOS Giovani | 17 | Barcelona (Spain) | (06-08) | £8,800,000 | MEX | Attacking Mid | Loan to Ipswich Town | 18 | 18 |
| X | CAMPBELL Fraizer | 18 | Manchester United | (09-08) | Season loan | E U21 | Striker | Season loan to May 2009 | 19 | 19 |
| 3 | TAARABT Adel | 19 | RC Lens (France) | (01-07) | £0? | MOR | Midfield | Loan to Queens Park Rgrs | 20 | 20 |
| 5 | DAWSON Michael | 20 | Nottingham Forest | (01-05) | £3,500,000 | ENG B | Defender | 21 | 21 | |
| 3 | CHIMBONDA Pascal | 21 | Sunderland | (01-09) | £3,000,000 | FRA | Defender | 22 | 22 | |
| X | SANCHEZ Cesar | 21 | Real Zaragoza (Spain) | (08-08) | Season loan | ESP | Goalkeeper | Valencia | 23 | 23 |
| X | CORKUKA Vedran | 22 | Manchester City | (09-08) | £8,500,000 | CRO | Defender | 24 | 24 | |
| X | CUDICINI Carlo | 23 | Chelsea | (01-09) | £0 | ITY U21 | Goalkeeper | 25 | 25 | |
| 2 | BOATENG Kevin-Prince | 23 | Hertha Berlin (Germany) | (07-07) | £4,500,000 | GER U21 | Midfield | Loan to Borussia Dortmund | 26 | 26 |
| 2 | O'HARA Jamie | 24 | Tottenham Youth | (12-06)* | £0 | E U21 | Left Def/Mid | 27 | 27 | |
| 6 | DEFOE Jermain | 25 | Portsmouth | (01-09) | £15,000,000 | ENG | Striker | 28 | 28 | |
| 11 | KING Ledley | 26 | Tottenham Youth | (05-99)* | £0 | ENG | Centre Half | 29 | 29 | |
| 3 | ALNWICK Ben | 27 | Sunderland | (01-07) | £1,300,000 | E U21 | Goalkeeper | 30 | 30 | |
| 3 | ASSOU-EKOTTO Benoit | 32 | RC Lens (France) | (07-06) | £3,500,000 | CAM | Left Def/Mid | 31 | 31 | |
| 3 | ROCHA Ricardo | 33 | Benfica (Portugal) | (01-07) | £3,276,000 | POR | Defender | 32 | 32 | |
| 2 | WOODGATE Jonathan | 39 | Middlesbrough | (01-08) | £7,000,000 | ENG | Centre Half | 33 | 33 | |
| X | BUTCHER Lee | Tottenham Youth | Goalkeeper | 1 | 34 | |||||
| x | JANSSON Oscar | 30 | Karlsund HFK (Sweden) | (07-08)* | £0 | SWE U18 | Goalkeeper | 2 | 35 | |
| X | BUTTON David | 56 | Tottenham Youth | E U19 | Goalkeeper | 3 | 36 | |||
| X | MTANDARI Takura | 65 | Tottenham Youth | Defender | 4 | 37 | ||||
| X | BERCHICHE Yuri | Athletico Bilbao (Spain) | (06-07) | £0? | ESP U17 | Left Back | 5 | 38 | ||
| X | HUGHTON Cian | 64 | Tottenham Youth | IRE U19 | Defender | 6 | 39 | |||
| X | ARCHIBALD-HENVILLE Troy | Tottenham Youth | (11-07)* | £0 | Defender | Season loan to Exeter City | 7 | 40 | ||
| 3 | DERVITE Dorian | 63 | Lille (France) | (07-06) | £250,000 | F U18 | Defender | Loan to Southend May 2009 | 8 | 41 |
| X | MILLS Leigh | 48 | Swindon Town | (07-04) | £80,000 | Defender | Released Feb 2009 | 9 | 42 | |
| X | HUTCHINS Danny | 71 | Tottenham Youth | Midfield | 10 | 43 | ||||
| X | HUTTON David | 72 | Tottenham Youth | IRL U19 | Midfield | 11 | 44 | |||
| X | DANIELS Charlie | Tottenham Youth | Midfield | Leyton Orient Jan 2009 | 12 | 45 | ||||
| X | McKENNA Kieran | 55 | Tottenham Youth | Midfield | 13 | 46 | ||||
| X | MAGHOMA Jacques | 76 | Tottenham Youth | Midfield | 14 | 47 | ||||
| X | ROSE Danny | 53 | Leeds United | (07-07) | £1,000,000 | ENG U18 | Midfield | 15 | 48 | |
| X | LIVERMORE Jake | 75 | Tottenham Youth | Midfield | 16 | 49 | ||||
| X | FRASER-ALLEN Kyle | 70 | Tottenham Youth | E U17 | Right Winger | 17 | 50 | |||
| X | DAWKINS Simon | 47 | Tottenham Youth | (10-07)* | £0 | Striker | Loan to Leyton Orient | 18 | 51 | |
| X | PEKHART Tomas | 46 | Slavia Prague (Czech Republic) | (07-06) | £250,000 | CZR U21 | Striker | Year loan to Slavia Feb 2010 | 19 | 52 |
| X | HAMED Radwan | Tottenham Youth | Striker | 20 | 53 | |||||
| 3 | BARCHAM Andy | 54 | Tottenham Youth | (11-06)* | £0 | E U16 | Striker | Gillingham January 2009 | 21 | 54 |
| X | OLSEN Alex | SK Gjovik Lynn (Norway) | NOR U18 | Striker | 22 | 55 | ||||
| X | DALTON James | 58 | Tottenham Youth | Goalkeeper | 1 | 56 | ||||
| X | BUTCHER Calum | 59 | Tottenham Youth | Goalkeeper | 2 | 57 | ||||
| X | SHEHU Ajet | Tottenham Youth | Defender | 3 | 58 | |||||
| X | SMITH Adam | 67 | Tottenham Youth | (07-08)* | £0 | E U16 | Defender | 4 | 59 | |
| X | CLARE Mark | 61 | Tottenham Youth | Defender | 5 | 60 | ||||
| X | KASIM Yasir | 73 | Tottenham Youth | Midfield | 6 | 61 | ||||
| X | COX Samuel | 62 | Tottenham Youth | Midfield | 7 | 62 | ||||
| X | MASON Ryan | 77 | Tottenham Youth | Midfield | 8 | 63 | ||||
| X | ASAJILE Saulo | Tottenham Youth | Midfield | 9 | 64 | |||||
| X | TOWNSEND Andros | 81 | Tottenham Youth | (07-08)* | £0 | Midfield/Attack | 10 | 65 | ||
| X | OBIKA Jonathan | 80 | Tottenham Youth | Striker | 11 | 66 | ||||
| X | RANIERI Mirko | Perugia (Italy) | ITY U16 | Goalkeeper | 1 | 67 | ||||
| X | BUTLER James | 57 | Tottenham Youth | Goalkeeper | 2 | 68 | ||||
| X | CAULKER Steven | Tottenham Youth | Defender | 3 | 69 | |||||
| X | BYRNE Nathan | 60 | Tottenham Youth | Defender | 4 | 70 | ||||
| X | PARRETT Dean | 52 | Queens Park Rangers | E U16 | Midfield | 5 | 71 | |||
| X | O'NEILL Chance | Tottenham Youth | Midfield | 6 | 72 | |||||
| X | KANE Harry | Tottenham Youth | Attacking Mid | 7 | 73 | |||||
| X | NICHOLSON Jake | 78 | Tottenham Youth | Midfield | 8 | 74 | ||||
| X | EKIM Coskum | 69 | Tottenham Youth | Midfield | 9 | 75 | ||||
| X | CARROLL Thomas | 68 | Tottenham Youth | Midfield | 10 | 76 | ||||
| X | BOSTOCK John | 51 | Crystal Palace | (05-08) | £2,150,000 | E U16 | Midfield | 11 | 77 | |
| X | MPUKU Paul-Jose | Standard Liege (Belgium) | (06-08) | £0? | BEL U16 | Striker | 12 | 78 | ||
| X | JACK Anthony | 79 | Tottenham Youth | Midfield/Attack | 13 | 79 | ||||
| £192,961,000 | ||||||||||