Results
- 2 September 1899Chesham TownSouthern League Division 2AwayLost 0–4
- 9 September 1899BrentfordSouthern League Division 2AwayLost 0–1
- 16 September 1899WandsworthFriendly : 1st TeamHomeWon 5–3
- 23 September 1899SouthallSouthern League Division 2AwayWon 2–0
- 30 September 1899Crouch End VampiresFriendly : 1st TeamHomeWon 5–3
- 7 October 1899Wolverton L.& N.W.R.Southern League Division 2HomeWon 3–1
- 14 October 1899Bowes ParkFriendly : 1st TeamHomeWon 7–1
- 21 October 1899SloughF.A. Amateur Cup · 1QHomeWon 3–1
- 28 October 1899ReadingF.A. Challenge Cup · 3QHomeLost 0–8
- 4 November 1899MaidenheadF.A. Amateur Cup · 2QAwayWon 6–0
- 11 November 1899Shepherds BushSouthern League Division 2HomeWon 2–1
- 18 November 1899Oxford CityF.A. Amateur Cup · 3QHomeWon 2–0
- 25 November 1899WatfordSouthern League Division 2HomeWon 2–1
- 2 December 1899Aylesbury UnitedBerks & Bucks Senior Cup (1) · Round 2AwayWon 2–1
- 9 December 1899Reading AmateursF.A. Amateur Cup · 4QAwayWon 3–0
- 26 December 1899Civil ServiceFriendly : 1st TeamHomeWon 3–2
- 29 December 1899MarlowFriendly : 1st TeamHomeWon 2–1
- 6 January 1900MaidenheadSouthern League Division 2HomeWon 6–0
- 13 January 1900Grays UnitedSouthern League Division 2HomeDrawn 2–2
- 20 January 1900MarlowF.A. Amateur Cup · Round 1HomeDrawn 1–1
- 27 January 1900MarlowF.A. Amateur Cup · Round 1 RepAwayLost 0–1
- 24 February 1900SouthallSouthern League Division 2HomeWon 1–0
- 3 March 1900Maidenhead NorfolkiansBerks & Bucks Senior Cup (1) · S/FNeutralWon 3–1
- 10 March 1900WatfordSouthern League Division 2AwayLost 0–1
- 17 March 1900MaidenheadSouthern League Division 2AwayWon 1–0
- 21 March 1900DartfordSouthern League Division 2HomeWon 6–1
- 24 March 1900Maidenhead NorfolkiansMaidenhead Norfolkian Charity Cup (1) · Round 1HomeWon 3–0
- 31 March 1900Shepherds BushSouthern League Division 2AwayLost 2–3
- 7 April 1900Chesham TownSouthern League Division 2HomeDrawn 5–5
- 14 April 1900FulhamSouthern League Division 2AwayLost 0–2
- 16 April 1900MarlowBerks & Bucks Senior Cup (1) · FNeutralDrawn 1–1
- 18 April 1900DartfordSouthern League Division 2AwayLost 0–6
- 21 April 1900Wolverton L.& N.W.R.Southern League Division 2AwayLost 0–5
- 23 April 1900MarlowBerks & Bucks Senior Cup (1) · F RepNeutralLost 3–4
- 25 April 1900FulhamSouthern League Division 2HomeLost 0–6
- 28 April 1900Grays UnitedSouthern League Division 2AwayLost 0–9
- 30 April 1900BrentfordSouthern League Division 2HomeDrawn 2–2
Other teams (27 matches)
- 16 September 1899BurnhamSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayLost 2–5
- 23 September 1899Maidenhead Norfolkians ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamHomeWon 2–0
- 30 September 1899LoudwaterSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayDrawn 2–2
- 14 October 1899Eton WickSouth Bucks & East Berks Junior League (2) · 2nd TeamHomeWon 4–3
- 21 October 1899Marlow ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayAbandoned
- 4 November 1899Slough ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamHomeWon 8–0
- 11 November 1899Wycombe Marsh GordonsFriendly : 2nd Team · 2nd TeamAwayDrawn 0–0
- 18 November 1899Wooburn St Paul'sBerks & Bucks Junior Cup (2) · Round 2 · 2nd TeamAwayWon 9–1
- 25 November 1899StokenchurchFriendly : 2nd Team · 2nd TeamAwayWon 3–1
- 2 December 1899Wycombe AlexandraHigh Wycombe Challenge Cup (2) · Round 1 · 2nd TeamHomeWon 3–1
- 10 December 1899AmershamBerks & Bucks Junior Cup (2) · Round 3 · 2nd TeamAwayLost 1–2
- 17 December 1899Maidenhead Norfolkians ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayWon 5–1
- 25 December 1899Wooburn St Paul'sSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayWon 10–0
- 26 December 1899Princes Risborough TownFriendly : 2nd Team · 2nd TeamAwayWon 6–2
- 6 January 1900Maidenhead ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayWon 2–1
- 13 January 1900Slough ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayLost 1–5
- 27 January 1900AmershamHigh Wycombe Challenge Cup (2) · Round 2 · 2nd TeamHomeWon 6–1
- 3 March 1900Chesham Generals ReservesHigh Wycombe Challenge Cup (2) · S/F · 2nd TeamAwayDrawn 0–0
- 10 March 1900Chesham Generals ReservesHigh Wycombe Challenge Cup (2) · S/F R · 2nd TeamHomeWon 2–1
- 17 March 1900Maidenhead ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamHomeWon 5–0
- 24 March 1900Marlow ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayLost 1–4
- 7 April 1900Reading RamblersMaidenhead Norfolkian Charity Cup (2) · S/F · 2nd TeamAwayLost 1–10
- 14 April 1900LoudwaterSouth Bucks & East Berks Junior League (2) · 2nd TeamHomeDrawn 0–0
- 18 April 1900Marlow ReservesSouth Bucks & East Berks Junior League (2) · 2nd TeamHomeWon 2–0
- 19 April 1900BurnhamSouth Bucks & East Berks Junior League (2) · 2nd TeamHomeWon 2–1
- 21 April 1900LoudwaterHigh Wycombe Challenge Cup (2) · F · 2nd TeamHomeWon 5–0
- 28 April 1900Eton WickSouth Bucks & East Berks Junior League (2) · 2nd TeamAwayDrawn 1–1
League table
Southern League Division Two · 11 teams · Open in League tables
| Pos | Team | P | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Prom | 20 | 14 | 2 | 4 | 57 | 25 | +32 | 30 |
| 2 | 20 | 10 | 4 | 6 | 44 | 23 | +21 | 24 | |
| 3 | 20 | 11 | 2 | 7 | 43 | 37 | +6 | 24 | |
| 4 | left | 20 | 9 | 6 | 5 | 46 | 36 | +10 | 24 |
| 5 | 20 | 8 | 6 | 6 | 63 | 29 | +34 | 22 | |
| 6 | 20 | 9 | 4 | 7 | 45 | 37 | +8 | 22 | |
| 7 | left | 20 | 8 | 3 | 9 | 36 | 44 | -8 | 19 |
| 8 | Wycombe Wanderers | 20 | 8 | 3 | 9 | 35 | 50 | -15 | 19 |
| 9 | 20 | 5 | 7 | 8 | 31 | 48 | -17 | 17 | |
| 10 | 20 | 6 | 3 | 11 | 21 | 44 | -23 | 15 | |
| 11 | 20 | 1 | 2 | 17 | 16 | 64 | -48 | 4 |