30 August 1999

Stevenage Borough 3-0 Kettering Town

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28 August 1999

Scarborough 1-3 Stevenage Borough

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24 August 1999

Sutton United 0-2 Stevenage Borough

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21 August 1999

Stevenage Borough 2-0 Telford United

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16 August 1999

Stevenage Borough 3-0 Doncaster Rovers

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14 August 1999

Altrincham 0-1 Stevenage Borough

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01 May 1999

Yeovil Town 1-3 Stevenage Borough

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24 April 1999

Stevenage Borough 3-0 Kidderminster Harriers

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19 April 1999

Hednesford Town 2-2 Stevenage Borough

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17 April 1999

Stevenage Borough 1-2 Barrow

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