In 1899, the VFL competition consisted of eight teams of 18 on-the-field players each, with no "reserves" (although any of the 18 players who had left the playing field for any reason could later resume their place on the field at any time during the match).

Each team played each other twice in a home-and-away season of 14 rounds.

Once the 14 round home-and-away season had finished, the 1899 VFL Premiers were determined by the specific format and conventions of the 1898 VFL Premiership System.

Round 1 edit

Round 2 edit

Round 3 edit

Round 4 edit

Round 5 edit

Round 6 edit

Round 7 edit

Round 8 edit

Round 9 edit

Round 10 edit

Round 11 edit

Round 12 edit

Round 13 edit

Round 14 edit

Rules for classification: 1. premiership points; 2. percentage; 3. points for
Average score: 37.5
Source: AFL Tables

Ladder progression edit

• No ladder for finals in 1899.

Sectional rounds edit

Sectional round 1 edit

Sectional round 2 edit

Sectional round 3 edit

Section A ladder edit

Rules for classification: 1. premiership points; 2. percentage; 3. points for
Source: AFL Tables

Section B ladder edit

Rules for classification: 1. premiership points; 2. percentage; 3. points for
Source: AFL Tables

Grand final edit

Starting time is local time. Source: AFL Tables

The following table can be sorted from biggest winning margin to biggest losing margin for each round. If two or more matches in a round are decided by the same margin, these margins are sorted by percentage (i.e. the lowest-scoring winning team is ranked highest and the lowest-scoring losing team is ranked lowest). Opponents are listed above the margins and home matches are in bold.

Source: AFL Tables

• The VFL reduced the size of its teams from 20 to 18 on-the-field players, with no "reserves". In doing this, the number of followers was reduced from five (four rucks and a rover) to three (two rucks and a rover).^[1]
• The third round, Queen's Birthday holiday match, between Collingwood and St Kilda at Victoria Park was held in the morning of Wednesday 24 May 1899.
• Norman "Hackenschmidt" Clark, a footballer with the North Adelaide Football Club in the South Australian Football Association, won the 1899, 130-yard Stawell Gift in eleven and four-fifths seconds, off a handicap of 14 and a half yards. Clark would later play 125 senior games for Carlton (1905–1912), captain-coach VFA team Brighton (1913), and coach Carlton (1914–1918; 1920–1922), Richmond (1919), North Melbourne (1924 and 1931) and St Kilda (1925–1926).
• At half-time of the Round 13 game between Fitzroy and Collingwood, Fitzroy captain Alec Sloan offers Collingwood captain Dick Condon the use of a fresh football, due to the old ball being greasy. Condon declines, and Colingwood win the game 5.7 (37) to 3.7 (25).
• The first seven kicks of the Round 14 game between Carlton and Fitzroy are free kicks awarded by the umpire.
• In the third sectional round, Geelong set records for the highest score in a game, scoring 23.24 (162), and the highest winning margin of 161 points, against St Kilda. These records would both stand for twelve years and twenty years respectively.
• St Kilda's score of 0.1 (1) in the same match set the record for the lowest score in a VFL/AFL game, which has neither been matched nor broken since. Notably, the solitary behind was actually the first score of the match.
• Geelong's Jim McShane kicked 11 goals in the same match against St Kilda, a VFL record that was not equalled until Collingwood's Dick Lee's 11 goals in 1914 and not broken until 1922; this is more impressive considering that McShane was usually a ruckman.
• Warwick Armstrong (6'3", 190 cm), later captain of the Australian Test Cricket team, played in the ruck for the South Melbourne team that lost the 1899 "Grand Final".
• At the end of the 1899 season, in the process of naming his own "champion player", the football correspondent for The Argus ("Old Boy"), selected a team of the best players of the 1899 VFL competition:
  Backs: Maurie Collins (Essendon), Bill Proudfoot (Collingwood), Peter Burns (Geelong); Halfbacks: Pat Hickey (Fitzroy), George Davidson (South Melbourne), Alf Wood (Melbourne); Centres: Fred Leach (Collingwood), Firth McCallum (Geelong), Harry Wright (Essendon); Wings: Charlie Pannam (Collingwood), Eddie Drohan (Fitzroy), Herb Howson (South Melbourne); Forwards: Bill Jackson (Essendon), Eddy James (Geelong), Charlie Colgan (South Melbourne); Ruck: Mick Pleass (South Melbourne), Frank Hailwood (Collingwood), Joe McShane (Geelong); Rovers: Dick Condon (Collingwood), Bill McSpeerin (Fitzroy), Teddy Rankin (Geelong).
  From those he considered to be the three best players — that is, Condon, Hickey, and Pleass — he selected Pat Hickey as his "champion player" of the season. ('Old Boy', "Football: A Review of the Season", (Monday, 18 September 1899), p.6).

• The 1899 VFL Premiership team was Fitzroy.
• The VFL's leading goalkicker was Eddy James of Geelong with 31 goals.
• The Argus newspaper's "Player of the Year" was Fitzroy's Pat Hickey.

• Rogers, S. & Brown, A., Every Game Ever Played: VFL/AFL Results 1897–1997 (Sixth Edition), Viking Books, (Ringwood), 1998. ISBN 0-670-90809-6
• Ross, J. (ed), 100 Years of Australian Football 1897–1996: The Complete Story of the AFL, All the Big Stories, All the Great Pictures, All the Champions, Every AFL Season Reported, Viking, (Ringwood), 1996. ISBN 0-670-86814-0

• 1899 VFL season at AFL Tables
• 1899 VFL season at Australian Football