The draw for the 2nd Round of the Cornwall Senior Cup to be played on Saturday, 20 November 1999, kick-off 2.30p.m. resulted as follows:

Bodmin Town v Kelly Bray Athletic, Bude Town v Millbrook, Callington Town v Torpoint Athletic, Camelford v Ludgvan, Foxhole Stars v Sticker, Helston Athletic v Illogan RBL, Launceston v Goonhaven Athletic or Troon, Mousehole v Padstow Utd, Mullion v Porthleven, Perranwell v Wadebridge Town, Saltash Utd v Newquay, St Agnes or Nanpean v St Blazey, St Austell v Penzance, St Dennis or St Ives v Falmouth Town, St Just v Liskeard Athletic, Truro City v Probus.

The draw for the 2nd Round of the Durning Lawrence Charity Cup to be played by Monday, 28th February 2000 resulted as follows:

St Blazey v Millbrook, Penryn Athletic v Penzance, Porthleven v Newquay, Falmouth Town v Saltash Utd.