| Tournament details | |
|---|---|
| Country | Singapore | 
| Dates | April 2009 - November 2009 | 
| Teams | 16 | 
| Final positions | |
| Champions | Geylang United | 
| Runner-up |  Bangkok Glass | 
The Singapore Cup 2009 (known as the RHB Singapore Cup due to its main sponsor) started on 27 April 2009. It was the 12th staging of the annual Singapore Cup tournament.
12 S.League clubs and 4 invited foreign teams from Thailand (2 teams), Cambodia (1) and Indonesia (1) played in this edition. The cup was a single-elimination tournament, with all sixteen teams playing from the first round. The first round involved one-off matches. Subsequent rounds involved ties of two legs.
The final was played on 8 November and won by Geylang United, who beat Bangkok Glass 1–0.
The cup winner were guaranteed a place in the 2010 AFC Cup.
Teams
Knockout stage
The draw for the tournament was held on 15 April 2009
Bracket
| Round of 16 | Quarter-finals | Semi-finals | Final | ||||||||||||||||
| Tampines Rovers | 1 | ||||||||||||||||||
| Sengkang Punggol | 0 | ||||||||||||||||||
| Tampines Rovers | 1 | 0 | 1 (1) | ||||||||||||||||
|  Albirex Niigata (S) | 0 | 1 | 1 (3) | ||||||||||||||||
|  Albirex Niigata (S) | 3 | ||||||||||||||||||
| Gombak United | 1 | ||||||||||||||||||
|  Albirex Niigata (S) | 0 | 1 | 1 (3) | ||||||||||||||||
| Geylang United | 1 | 0 | 1 (4) | ||||||||||||||||
| Geylang United | 2 | ||||||||||||||||||
| SAFFC | 1 | ||||||||||||||||||
| Geylang United | 2 | 2 | 4 | ||||||||||||||||
| Home United | 1 | 2 | 3 | ||||||||||||||||
| Balestier Khalsa | 0 | ||||||||||||||||||
| Home United | 3 | ||||||||||||||||||
| Geylang United | 1 | ||||||||||||||||||
|  Bangkok Glass | 0 | ||||||||||||||||||
|  TTM Samut Sakhon | 4 | ||||||||||||||||||
|  Super Reds | 2 | ||||||||||||||||||
|  TTM Samut Sakhon | 3 | 4 | 7 | ||||||||||||||||
|  DPMM FC | 1 | 2 | 3 | ||||||||||||||||
|  DPMM FC | 1 | ||||||||||||||||||
|  Pelita Jaya | 0 | ||||||||||||||||||
|  TTM Samut Sakhon | 0 | 4 | 4 | ||||||||||||||||
|  Bangkok Glass | 6 | 3 | 9 | ||||||||||||||||
|  Phnom Penh Crown | 2 | ||||||||||||||||||
| Young Lions | 0 | ||||||||||||||||||
|  Phnom Penh Crown | 1 | 3 | 4 | ||||||||||||||||
|  Bangkok Glass | 2 | 3 | 5 | ||||||||||||||||
| Woodlands Wellington | 0 | ||||||||||||||||||
|  Bangkok Glass | 1 | ||||||||||||||||||
Preliminary round
|  DPMM FC | 1 – 0 |  Pelita Jaya | 
|---|---|---|
| Abdelhamid Berguiga  76' | Details Report | 
| Balestier Khalsa | 0 – 3 | Home United | 
|---|---|---|
| Sofiyan Abdul Hamid  90' | Details Report | Norikazu Murakami  10' Shahril Ishak  15' Kengne Ludovick  38' | 
| Geylang United | 2 – 1 | SAFFC | 
|---|---|---|
| Yasir Hanapi  29' Syed Thaha  62' | Details Report | Therdsak Chaiman  90' | 
|  Albirex Niigata (S) | 3 – 1 | Gombak United | 
|---|---|---|
| Kenji Adachihara  54' Keisuke Ogawa  70' (pen) Akira Takase  90' | Details Report | Bah Mamadou  83' Jaslee Hatta  40' | 
|  Phnom Penh Crown | 2 – 0 |  Young Lions FC | 
|---|---|---|
| Jean Lappe Lappe  25'  60' | Details Report | 
|  TTM Samut Sakhon | 4 – 2 |  Super Reds | 
|---|---|---|
| Paul Bekombo  7'  84' Narong Jansawek  53' Aly Camara  90' | Details Report | Yun Bo-Young  51' (pen) Park Han Seok  78' | 
Quarter-finals
First leg
|  Phnom Penh Crown | 1 – 2 |  Bangkok Glass | 
|---|---|---|
| Chan Chaya  8' | Details Report | Chatree Chimtalay  39' Metee Pungpoh  53' | 
|  DPMM FC | 1 – 3 |  TTM Samut Sakhon | 
|---|---|---|
| Abu Bakar Mahari  76' | Details Report | Paul Bekombo  16'  61' Aly Camara  89' | 
| Geylang United | 2 – 1 | Home United | 
|---|---|---|
| Noor Ali  48' Baihakki Khaizan  65' (pen.) | Details Report | Valery Hiek  23'  64' | 
Second leg
|  TTM Samut Sakhon | 4 – 2 |  DPMM FC | 
|---|---|---|
| Aly Camara  1' Pradit Taweechai  26' Tanongsak Promdard  83' Saksit Wuttipadadorn  89' | Details Report | Abdelhamid Berguiga  88' Ivan Jerkovic  90' | 
TTM Samut Sakhon won 7 – 3 on aggregate.
|  Bangkok Glass | 3 – 3 |  Phnom Penh Crown | 
|---|---|---|
| Nelson San Martín  13' Nantawat Tansopa  16' Surachet Ngamtip  37' | Details Report | Chan Rithy  20' (pen.) Keo Sokngon  32' Marcel Modibo  55' | 
Bangkok Glass won 5 – 4 on aggregate.
| Home United | 2 – 2 | Geylang United | 
|---|---|---|
| Tengku Mushadad  45' Peres De Oliveira  89' (pen.) | Details Report | Miroslav Latiak  11' Masrezwan Masturi  84' | 
Geylang United won 4 – 3 on aggregate.
|  Albirex Niigata (S) | 1 – 0 | Tampines Rovers | 
|---|---|---|
| Kenji Adachihara  90' | Details Report | Benoit Croissant  85' | 
| Penalties | ||
| Kenji Adachihara   Ken Matsumoto   Ryohei Maeda   Kazuki Yoshino  | 3 – 1 |  Sutee Suksomkit  Mustafic Fahrudin  Zulkarnaen Zainal  Fathi Yunus | 
Albirex Niigata (S) 1 – 1 Tampines Rovers on aggregate. Albirex Niigata (S) won 3 – 1 on penalties.
Semifinals
First leg
|  Albirex Niigata (S) | 0 – 1 | Geylang United | 
|---|---|---|
| Tetsuya Kishida  73'  87' | Details Report | Kim Jae-Hong  61' | 
|  TTM Samut Sakhon | 0 – 6 |  Bangkok Glass | 
|---|---|---|
| Details Report | Ajayi Samuel  1'  11'  72' Sarun Promkaew  5' Tanat Wongsuparak  34' Rungroj Sawangsri  52' (pen.) | 
Second leg
| Geylang United | 0 – 1 |  Albirex Niigata (S) | 
|---|---|---|
| Details Report | Taisuke Akiyoshi  42' | |
| Penalties | ||
| Kim Jae-Hong   Faizal Senin   Miroslav Latiak   Walid Lounis  | 4 – 3 |  Kazuki Yoshino  Kenji Adachihara  Taisuke Akiyoshi  Akira Takase  Yoshitaka Komori | 
Geylang United 1 – 1 Albirex Niigata (S) on aggregate. Geylang United won 4-3 on penalties.
|  Bangkok Glass | 3 – 4 |  TTM Samut Sakhon | 
|---|---|---|
| Chatree Chimtalay  6'  86' Peeratat Phoruendee  71' (o.g.) Wachira Sangsri  90' | Details Report | Supphakorn Ramkulabsuk  8' Paul Bekombo  20' (pen.)  62' Worawut Wangsawad  90' (pen.) Camara Aly  75'  75' | 
Bangkok Glass won 9 – 4 on aggregate.
Third Place Playoff
|  Albirex Niigata (S) | 1 – 1 |  TTM Samut Sakhon | 
|---|---|---|
| Kunihiro Honda  89' | Details Report | Tanongsak Promdard  20' | 
| Penalties | ||
| Kazuki Yoshino   Ken Matsumoto   Ryohei Maeda   Kunihiro Honda   Akira Takase  | 3 – 4 |  Worawut Wangsawad  Tana Sripandorn  Tanongsak Prajakkata  Narong Jansawek  Paul Bekombo | 
Final
| Geylang United | 1 – 0 |  Bangkok Glass | 
|---|---|---|
| Hafiz Rahim  82' | Details Report | 
|       Geylang United |       Bangkok Glass | 
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