The 2009 Cities' Cup season was the fifth edition of the Cities' Cup, the secondary football cup competition in Craitland. The cup was contested by 18 teams, and was held between December 2008 and May 2009.
The final was won by TTC Tiem FC, who beat CT United FC 3–2 for their first ever title.
Qualifying round
- Group A
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| FC K'eĵer |
2 – 0 |
K'aĵräk Phoenixes FC
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| K'aĵräk Phoenixes FC |
1 – 1 |
Yaärl Kahthajtensen FC
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| FC K'eĵer |
0 – 0 |
Yaärl Kahthajtensen FC
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- Group B
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| Hänä Mountain Rangers FC |
2 – 2 |
K'asan XI FC
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| K'asan XI FC |
2 – 0 |
M'e-D'aar FC
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| Hänä Mountain Rangers FC |
2 – 1 |
M'e-D'aar FC
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First round
Quarter-finals
Semi-finals
Final
 Craitland Football Association |
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| | National team (statistics · Golden Generation) · U-21 national team · Women's national team · CÓNECT · Player of the Year | | | | | CrFA clubs |
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| | League 1 | Biulya äqi Jedu FC ( seasons, players) · Cherry Trees FC ( seasons, players) · Eĵars Town FC ( seasons, players) · Hänävissen-ó-Cräiteland FC ( seasons, players) · Kealb FC ( seasons, players) Osĵätoņ Aztecs FC ( seasons, players) · Róndlinga Diamonds FC ( seasons, players) · Sverige Tiem FC ( seasons, players) · Xäiville Teflons FC ( seasons, players) · Zekäbelóman Kahthajtensen FC ( seasons, players) | | | League 2 | | | | League 3 | |
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