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Chesterfield historical cup results 1987/1988

Full listing of knockout competition results during the season

View Chesterfield's results from other seasons
The F.A. Cup
 1st RoundSun 15 NovNotts. County (DIV3)3 - 3Chesterfield (DIV3) 
 1st Round ReplayTue 17 NovChesterfield (DIV3)0 - 1Notts. County (DIV3) 
Littlewoods League Cup
 1st Round 1st LegTue 18 AugChesterfield (DIV3)2 - 1Peterborough (DIV4) 
 1st Round 2nd LegWed 26 AugPeterborough (DIV4)2 - 0Chesterfield (DIV3) 
Peterborough United won 3-2 on aggregate
Sherpa Van Trophy (Associate Members)
 Northern Section Preliminary Round Group FiveTue 24 NovChesterfield (DIV3)2 - 0York City (DIV3) 
 Northern Section Preliminary Round Group FiveSat 05 DecDarlington (DIV4)2 - 1Chesterfield (DIV3) 
 Northern Section 1st RoundTue 19 JanHalifax Town (DIV4)2 - 1Chesterfield (DIV3) 
after extra time, 90 minutes 1-1