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 | 27/08/2008 - League Managers Meeting - Sale FC | |
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| 07/09/2008 - Rhyl 22 v Caldy 48 | |
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| 14/09/2008 - Penrith 43 - Caldy 7 | |
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| 21/09/2008 - Caldy 22 - Stockport 24 | |
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| 28/09/2008 - Northwich 28 - Caldy 29 | |
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| 05/10/2008 - Caldy 108 - Preston Grasshoppers 30 | |
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| 12/10/2008 - Ormskirk 27 - Caldy 26 | |
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| 19/10/2008 - Caldy 22 - Wirral 23 | |
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| 09/11/2008 - Wirral 12 - Caldy 6 | |
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| 16/11/2008 - Caldy 17 - Ormskirk 36 | |
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| 23/11/2008 - Preston Grasshoppers 0 - Caldy 41 | |
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| 30/11/2008 - County Cup 1st Round | |
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| 07/12/2008 - Caldy 18 - Northwich 10 | |
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| 14/12/2008 - Stockport 7 - Caldy 14 | |
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| 21/12/2008 - Caldy 20 - Penrith 17 | |
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| 28/12/2008 - Weather Weekend | |
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| 04/01/2009 - Caldy v Rhyl | |
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| 11/01/2009 - Weather Weekend | |
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| 11/01/2009 - Fleetwood 22 - Caldy 22 |   |
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| 18/01/2009 - Lymm 16 - Caldy 19 | |
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| 25/01/2009 - Weather Weekend | |
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| 25/01/2009 - Caldy 19 - Lymm 43 | |
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| 01/02/2009 - County Cup 2nd Round | |
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| 08/02/2009 - Caldy 33 - Fleetwood 13 | |
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| 15/02/2009 - Weather Weekend | |
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| 22/02/2009 - League Cup & Plate - Preliminary Round | |
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| 01/03/2009 - Weather Weekend | |
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| 08/03/2009 - League Cup & Plate - 1st Round | |
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| 15/03/2009 - Weather Weekend | |
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| 22/03/2009 - League Cup & Plate - 2nd Round | |
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| 29/03/2009 - League Cup & Plate - Semi Finals | |
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| 05/04/2009 - County Cup Semi Finals | |
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| 12/04/2009 - Weather Weekend | |
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| 19/04/2009 - Weather Weekend | |
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| 26/04/2009 - League Cup & Plate - Finals | |
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| 03/05/2009 - County Cup Finals | |
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| 15/05/2009 - League Presentation Evening - Sale FC | |
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