| Season: | 1929–30 |
| Chairman: | Jack Knight |
| League Result: | 21st |
| Cup1 Result: | First round |
| League Topscorer: | Fred Cheesmur (17) |
| Season Topscorer: | Fred Cheesmur (17) |
| Highest Attendance: | tbc |
| Lowest Attendance: | tbc |
| Pattern La1: | _black_stripes |
| Pattern B1: | _blackstripes |
| Pattern Ra1: | _black_stripes |
| Socks1: | 000000 |
| Prevseason: | 1928–29 |
| Nextseason: | 1930–31 |
During the 1929–30 English football season, Gillingham F.C. competed in the Football League Third Division South. It was the 10th season in which the club competed in the Football League. Gillingham finished 21st and the club was required to apply for re-election to the League. The team lost in the first round of the FA Cup to Margate of the Kent League.
Forward Fred Cheesmur scored six goals in a match against Merthyr Town on 26 April 1930, a club record haul for a single match at a professional level which stands to this day.
The 1929 - 30 season was Gillingham's 10th season playing in the Football League; the club had been one of the founder members of the Third Division in 1920, which had been re-branded the Third Division South a year later when a parallel Third Division North was created. Gillingham had consistently struggled in the Third Division South and only once finished in the top half of the league table; in the 1928–29 season, the team had finished bottom and been required to apply for re-election to the Football League. Shortly afterwards, former Gillingham player Dick Hendrie, who had most recently served as assistant manager at Brentford, was appointed as Gillingham's new manager, replacing Albert Hoskins, who had resigned in late March.
Hendrie signed nearly an entire team of new players, including half-back Jack Beacham and teenaged forward Thomas Brennan from his former club Brentford. Four players joined from Scottish clubs, including goalkeeper Dave Smith from Hamilton Academical and full back John Geddes from Celtic. Half-backs Albert Collins and George Bishop were signed from Millwall and Merthyr Town respectively. New forwards joining the club included Fred Castle from Chesterfield and Fred Cheesmur from Charlton Athletic, as well as Jim McCafferty from minor Scottish club Shieldmuir Celtic and Campbell Whyte from Third Lanark.
Gillingham's first match of the season was at home to Walsall at Priestfield Road. New signings Smith, Beacham, Collins, Bishop, McCafferty, Cheesmur and Castle all made their debuts. Castle and Cheesmur scored the goals in a 2 - 1 victory for Gillingham. The attendance of 8,160 would prove to be the largest crowd of the season at Priestfield Road.
In the penultimate game of the season, Gillingham beat Merthyr Town 6 - 0; Cheesmur scored all the goals. It was the first time a Gillingham player had scored as many goals in a single game at a professional level and a record that stands to this day. The final match of the season was at home to Luton Town; Cheesmur and John Speed scored in a 2 - 0 win. Gillingham had ended the season with an unbeaten run of six games, comprising four wins and two draws, but still finished 21st in the division, ahead of only Merthyr Town.
Key
Results
| scope=col | Date | scope=col | Opponents | scope=col | Result | scope=col class=unsortable | Goalscorers | scope=col | Attendance |
|---|---|---|---|---|---|---|---|---|---|
| 31 August 1929 | Walsall (H) | 2-1 | Castle, Cheesmur | 8160 | |||||
| 4 September 1929 | Exeter City (A) | 0-3 | 5297 | ||||||
| 7 September 1929 | Queens Park Rangers (A) | 1-2 | Cheesmur | 11875 | |||||
| 11 September 1929 | Exeter City (H) | 2-0 | Castle (2) | 4574 | |||||
| 14 September 1929 | Fulham (H) | 0-1 | 7901 | ||||||
| 16 September 1929 | Luton Town (A) | 0-2 | 7168 | ||||||
| 21 September 1929 | Norwich City (A) | 0-2 | 9981 | ||||||
| 28 September 1929 | Crystal Palace (H) | 1-1 | Dowell | 6818 | |||||
| 5 October 1929 | Plymouth Argyle (A) | 0-3 | 5777 | ||||||
| 12 October 1929 | Northampton Town (A) | 1-3 | Pateman | 10663 | |||||
| 19 October 1929 | Swindon Town (H) | 0-0 | 5597 | ||||||
| 26 October 1929 | Brighton (A) | 0-2 | 7504 | ||||||
| 2 November 1929 | Bristol Rovers (H) | 3-3 | Cheesmur, Collins, Pateman | 4794 | |||||
| 9 November 1929 | Brentford (A) | 1-2 | Cheesmur | 9603 | |||||
| 16 November 1929 | Clapton Orient (H) | 2-0 | Cheesmur (2) | 1889 | |||||
| 23 November 1929 | Coventry City (A) | 0-5 | 8755 | ||||||
| 7 December 1929 | Newport County (A) | 1-5 | Geddes | 1991 | |||||
| 14 December 1929 | Torquay Utd (H) | 0-2 | 3310 | ||||||
| 21 December 1929 | Merthyr Town (A) | 1-1 | Dowell | 1352 | |||||
| 25 December 1929 | Bournemouth (H) | 1-5 | Castle | 3954 | |||||
| 26 December 1929 | Bournemouth (A) | 2-1 | Durnion (2) | 11481 | |||||
| 28 December 1929 | Walsall (A) | 2-1 | Durnion, Dowell | 3568 | |||||
| 4 January 1930 | Queens Park Rangers (H) | 3-1 | Durnion, Whyte, Cheesmur | 5961 | |||||
| 11 January 1930 | Watford (H) | 1-2 | Whyte | 5562 | |||||
| 18 January 1930 | Fulham (A) | 1-2 | Dowell | 15196 | |||||
| 25 January 1930 | Norwich City (H) | 1-2 | Dowell | 3249 | |||||
| 1 February 1930 | Crystal Palace (A) | 1-5 | Whyte | 8783 | |||||
| 8 February 1930 | Plymouth Argyle (H) | 0-0 | 4905 | ||||||
| 15 February 1930 | Northampton Town (H) | 5-2 | Durnion (4), Cheesmur | 4665 | |||||
| 22 February 1930 | Swindon Town (A) | 0-3 | 3070 | ||||||
| 1 March 1930 | Brighton (H) | 2-2 | Durnion, Dowell | 5035 | |||||
| 8 March 1930 | Bristol Rovers (A) | 0-3 | 5011 | ||||||
| 15 March 1930 | Brentford (H) | 1-3 | Dowell | 6749 | |||||
| 22 March 1930 | Clapton Orient (A) | 0-2 | 9348 | ||||||
| 29 March 1930 | Coventry City (H) | 0-3 | 3865 | ||||||
| 5 April 1930 | Watford (A) | 1-4 | Brennan | 4787 | |||||
| 12 April 1930 | Newport County (H) | 5-0 | Ellis, Bethell, Cheesmur (2), Jones | 2743 | |||||
| 18 April 1930 | Southend Utd (H) | 1-0 | Jones | 7964 | |||||
| 19 April 1930 | Torquay Utd (A) | 1-1 | Bethell | 3472 | |||||
| 21 April 1930 | Southend Utd (A) | 0-0 | 9036 | ||||||
| 26 April 1930 | Merthyr Town (H) | 6-0 | Cheesmur (6) | 3513 | |||||
| 3 May 1930 | Luton Town (H) | 2-0 | Cheesmur, Speed | 4831 |
Gillingham entered the 1929–30 FA Cup in the first round, and were paired with Margate of the Kent League, who had progressed from the qualifying rounds for the first time. In what was seen as a significant upset, Gillingham lost 2 - 0 to their lower-level opponents and were eliminated from the competition.
| scope=col | Date | scope=col | Round | scope=col | Opponents | scope=col | Result | scope=col class=unsortable | Goalscorers | scope=col | Attendance |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 30 November 1929 | First | scope=row | Margate (H) | 0 - 2 | 4,150 |
Twenty-seven players made at least one appearance for Gillingham during the season. George Bishop and Fred Cheesmur made the most, each playing in 41 of the team's 43 competitive matches; four other players each played more than 30 times. Ronald Baird was the only player to make just one appearance; he played against Coventry City in March, but it would prove to be the only game of his professional career.
Thirteen players scored at least one goal for Gillingham during the season. Cheesmur was the top goalscorer with 17 goals; no other player reached double figures.
| Player | Third Division South | FA Cup | Total | ||||
|---|---|---|---|---|---|---|---|
| Apps | Goals | Apps | Goals | Apps | Goals | ||
| 1 | 0 | 0 | 0 | 1 | 0 | ||
| 9 | 0 | 0 | 0 | 9 | 0 | ||
| 35 | 0 | 1 | 0 | 36 | 0 | ||
| 20 | 0 | 0 | 0 | 20 | 0 | ||
| 12 | 2 | 0 | 0 | 12 | 2 | ||
| 40 | 0 | 1 | 0 | 41 | 0 | ||
| 7 | 1 | 0 | 0 | 7 | 1 | ||
| 16 | 4 | 0 | 0 | 16 | 4 | ||
| 40 | 17 | 1 | 0 | 41 | 17 | ||
| 36 | 1 | 0 | 0 | 36 | 1 | ||
| 22 | 7 | 0 | 0 | 22 | 7 | ||
| 19 | 9 | 1 | 0 | 20 | 9 | ||
| 20 | 1 | 0 | 0 | 20 | 1 | ||
| 11 | 1 | 1 | 0 | 12 | 1 | ||
| 32 | 0 | 1 | 0 | 33 | 0 | ||
| 12 | 2 | 0 | 0 | 12 | 2 | ||
| 2 | 0 | 1 | 0 | 3 | 0 | ||
| 14 | 0 | 1 | 0 | 15 | 0 | ||
| 7 | 2 | 0 | 0 | 7 | 2 | ||
| 30 | 0 | 1 | 0 | 31 | 0 | ||
| 2 | 0 | 0 | 0 | 2 | 0 | ||
| 2 | 0 | 0 | 0 | 2 | 0 | ||
| 20 | 0 | 1 | 0 | 21 | 0 | ||
| 6 | 1 | 0 | 0 | 6 | 1 | ||
| 24 | 3 | 0 | 0 | 24 | 3 | ||
| 21 | 0 | 1 | 0 | 22 | 0 | ||
| 2 | 0 | 0 | 0 | 2 | 0 |
As a result of finishing 21st, Gillingham were required to apply for re-election for the second consecutive season, but were again re-elected. In the following season, the team finished 16th in the Third Division South.