Please choose match for more details.
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| 12 July 2011 |
Northwood I | v. Carisbrooke High School Old Boys: | Northwood beat CHSOB by 72 runs |
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| 28 May 2011 |
Freshwater | v. Carisbrooke High School Old Boys: | Freshwater beat Carisbrooke Old Boys by 134 runs |
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| 18 May 2011 |
Northwood I | v. Carisbrooke High School Old Boys: | CHSOB beat Northwood by 8 wickets |
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| 8 June 2010 |
Northwood I | v. Carisbrooke High School Old Boys: | CHSOB beat Northwood by 60 runs |
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| 22 May 2010 |
Whitecroft | v. Carisbrooke High School Old Boys: | Whitecroft beat Carisbrooke High School Old Boys by 129 runs |
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| 9 May 2010 |
Ryde Cavaliers I | v. Carisbrooke High School Old Boys: | cavaliers won by 204 runs |
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| 27 April 2010 |
Northwood I | v. Carisbrooke High School Old Boys: | CHSOB beat Northwood by 2 runs |
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| 24 April 2010 |
Shanklin II | v. Carisbrooke High School Old Boys: | CHSOB beat Shanklin II by 4 wickets |
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| 15 April 2010 |
Freshwater | v. Carisbrooke High School Old Boys: | Freshwater beat Carisbrooke Old Boys by 8wkts |
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| 8 August 2009 |
Arreton | v. Carisbrooke High School Old Boys: | Arreton beat Carisbrooke Old Boys by 66 runs |
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| 5 August 2009 |
Northwood I | v. Carisbrooke High School Old Boys: | Northwood beat CHSOB by 20 runs |
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| 9 July 2009 |
Northwood I | v. Carisbrooke High School Old Boys: | Northwood beat CHSOB by 7 wickets |
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| 30 May 2009 |
Ventnor III | v. Carisbrooke High School Old Boys: | Carisbrooke HSOB beat Ventnor III by 1 wicket |
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| 26 May 2009 |
Carisbrooke High School Old Boys | v. Northwood I: | CHSOB beat Northwood by 9 wickets |
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| 16 April 2009 |
West Island | v. Carisbrooke High School Old Boys: | CHS Old Boys beat West Island by 13 runs |
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| 2 August 2008 |
Brading | v. Carisbrooke High School Old Boys: | Brading beat CHSOB by 27 runs |
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| 21 July 2008 |
Plessey I | v. Carisbrooke High School Old Boys: | Carisbrooke won by 7 wickets |
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| 5 July 2008 |
Carisbrooke High School Old Boys | v. Ryde Cavaliers II: | CHS Old Boys beat Ryde Cavaliers II by 8 wickets |
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| 26 June 2008 |
Shanklin Evergreens | v. Carisbrooke High School Old Boys: | CHS Old Boys beat Shanklin Evergreens by 4 wickets |
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| 24 June 2008 |
Carisbrooke High School Old Boys | v. St Helens: | CHS Old Boys beat St Helens by 35 runs |
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| 19 June 2008 |
Plessey I | v. Carisbrooke High School Old Boys: | CHS Old Boys beat Plessey by 7 wickets |
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| 12 June 2008 |
IW Health Associates | v. Carisbrooke High School Old Boys: | CHS Old Boys beat IW Health Associates by 94 runs |
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| 10 June 2008 |
Carisbrooke High School Old Boys | v. Newport Victoria: | CHS Old Boys beat Newport Victoria by 7 runs |
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| 7 June 2008 |
Niton | v. Carisbrooke High School Old Boys: | Match Conceded by Niton. |
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| 3 June 2008 |
St Helens | v. Carisbrooke High School Old Boys: | Match Cancelled. Pitch waterlogged. |
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| 29 May 2008 |
IW Health Associates | v. Carisbrooke High School Old Boys: | CHS Old Boys beat IW Health Associates by 7 wickets |
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| 27 May 2008 |
IW Prison Officers | v. Carisbrooke High School Old Boys: | Match Conceded by IW Prison Officers |
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| 22 May 2008 |
Ryde 49ers | v. Carisbrooke High School Old Boys: | CHS Old Boys beat Ryde 49ers by 4 wickets |
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| 20 May 2008 |
Carisbrooke High School Old Boys | v. GKN: | CHS Old Boys beat GKN by 62 runs |
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| 15 May 2008 |
Carisbrooke High School Old Boys | v. Newport Victoria: | CHS Old Boys beat Newport Victoria by 60 runs |
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| 13 May 2008 |
Carisbrooke High School Old Boys | v. St Helens: | CHS Old Boys beat St Helens by 7 wickets |
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| 8 May 2008 |
Shanklin Evergreens | v. Carisbrooke High School Old Boys: | CHS Old Boys beat Shanklin Evergreens by 6 wickets |
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| 6 May 2008 |
Carisbrooke High School Old Boys | v. IW Prison Officers: | CHS Old Boys beat IW Prison Officers by 138 runs |
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| 1 May 2008 |
Carisbrooke High School Old Boys | v. Binstead: | Match Cancelled. Pitch waterlogged. |
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| 30 April 2008 |
GKN | v. Carisbrooke High School Old Boys: | Match Cancelled. Pitch waterlogged. |
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| 23 April 2008 |
Plessey I | v. Carisbrooke High School Old Boys: | CHS Old Boys beat Plessey by 42 runs |
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| 4 June 2008 |
St Helens | v. Carisbrooke High School Old Boys: | Match cancelled pitch unfit |
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| 30 April 2008 |
GKN | v. Carisbrooke High School Old Boys: | Cancelled due to rain. |
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| 2 September 2007 |
Carisbrooke High School Old Boys | v. Newport II: | CHSOB won by 24 runs |
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| 12 August 2007 |
Ryde II | v. Carisbrooke High School Old Boys: | C.H.S. old boys won by 7 wickets |
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