All games played:

• September 2nd, 1899 — 2–1 v Gravesend United (-) (September 2nd, 1899)
• September 16th, 1899 — 1–5 v Bristol City (-) (September 16th, 1899)
• October 7th, 1899 — 1–6 v Millwall Athletic (-) (October 7th, 1899)
• October 21st, 1899 — 3–1 v Chatham Town (-) (October 21st, 1899)
• November 4th, 1899 — 1–3 v Sheppey United (-) (November 4th, 1899)
• December 2nd, 1899 — 0–4 v Portsmouth (-) (December 2nd, 1899)
• December 16th, 1899 — 1–6 v Tottenham Hotspur (-) (December 16th, 1899)

7 League games played at Brooklyn by Cowes Sports