Highett joined the then Federal District league in 1929 where it played in the junior section. In 1934 it entered a side in Division two in the days when the competition was conducted on a promotion and relegation system.
In 1936-37-38 the Bulldogs were runners-up then in 1939 it finally won the Premiership its one and only.
The run of success ended in 1945 when it became a senior section club. From then the record was not good – 405 games with 102 wins, 299 losses, 4 ties and the wooden spoon on 6 occasions. The Federal League still longed for the day when the Highett Football Club could be represented in a Senior Grand Final. In 23 seasons they battled hard but never made the grade.
In 1959 they had a great chance which slipped through it’s fingers and they ended the year in 6th place. Highett was in the heart of Federal territory and success would bolster the club and the whole competition. Battling on they had identical seasons in 1966-67, with 6 wins and 12 losses with similar percentages 74.9% – 76.2%.
In 1969 the club improved just missing the finals on percentage but with young enthusiastic players in seniors and reserves a better start was assured.
The 1970 season proved to be the greatest year the club had ever had with 5 teams making the final four, but still failed to win a premiership, losing to Springvale in the preliminary final
In 1971 the club made the decision to change coaches and appointed Sandringham’s Darrell MacKenzie as Captain/Coach. It was a move that paid off with the seniors winning the Premiership, the clubs first senior flag and the reserves finishing runners-up, and the club winning the Beckwith trophy for the second year in a row.
Season 1972 resulted in another Grand Final birth only to be beaten by Noble Park.
The 1973 season proved to be the most outstanding year the club experienced, fielding senior, reserve, under 18 and under 16 teams in the Federal League and three teams in the Chelsea Junior League (under 10’s, 12’s and under 14’s), with 5 out of 7 entering the finals, resulting in a senior and reserve premiership and the under 14’s finishing runners up.
The 1974 season again proved to be a remarkable achievement winning our second flag in a row. Unfortunately however this was Darrell MacKenzie’s last year as playing coach. The 5th XVIII gained all honours in the Chelsea League by winning firstly the lightning premiership and then the Grand Final,
From years 75-78 the club performed reasonably well, it was a rebuilding process, as players retired due to injuries and age, and experienced difficulty in maintaining  the pressures and costs involved.  The social club and clubroom extensions were underway and opened in 1976.
Season 1979 saw a complete change in administration with former players taking over the running of the club. George Allen from Port Melbourne was appointed playing coach and brought known players with him.  With former coaches in Bob Linnell and Darrell MacKenzie playing the club formed a very strong side to take out the premiership defeasting Clayrom.
1980 saw increasing costs and a lack of success with a big possibility the club may have to disband, however despite their bad financial situation people rallied to keep the club going.
1981 had the club battling on with little success and amalgamation discussions were held with Highett West Football Club.  Highett had a good ground and facilities but was short on players. Highett West had the players but poor conditions at their Peterson St Reserve.


In 1982 the club transferred to the South East Suburban Football League after the Federal League went into recess subsequently amalgamating with Highet West to become the Highett District Bulldogs wearing the Highett West colour of the blue and white hoops. 




The formation of the Oakleigh District Football Club.
THE BEGINNING.
Courtesy Steve Laffan


Only 4 years after the War, in late 1949, a meeting was held on the first floor of the Mechanics Institute Hall in Drummond Street Oakleigh.  The meeting was arranged by Jack Hogan and ‘Pop’ Holmes regarding the starting up an open age side to provide somewhere for all boys over 18, to continue on with their football careers.  With the demise of the Oakleigh United Football Club, the only other open age Club in the area, at the time, was the VFA Oakleigh, who were more interested in recruiting players from the VFL than locals.

Representatives from the Oakleigh VFA club were invited to attend, and present at the meeting were Messrs, P Ireland (President), G Smeaton (Coach), D Whiteside and G Beasley. When asked if the Oakleigh Football Club could contribute financial help to set up the new club Phil Ireland's reply was that Oakleigh did not have enough funds to help.  Nevertheless, the meeting decided to form the Oakleigh District Football Club anyway. It is somewhat ironic that sixty plus years later Oakleigh VFA is extinct and the Oakleigh District Football Club still survives.

In the following months much effort was spent chasing and interviewing prospective players and Committee members and the new Oakleigh District Football Club was accepted into the Caulfield-Oakleigh District Football League for Season 1950.



During these busy months, and for the second time, the Oakleigh VFA Club was asked to assist by donating a set of their used guernsey’s, but the answer was an emphatic ‘no.’ It was obvious that the Oakleigh VFA club were not in any way prepared to assist the new Club. 

A few disgruntled Committee members then went to the Oakleigh Sports Store, in Portman Street and asked owner Alan ‘Brud’ Laffan for the cheapest jumpers he had. It was a set of Collingwood guernseys (because there was so many of them available ) which he kindly donated, and so the Oakleigh Districts Football Club became the Magpies and Brud Laffan became the Club’s first President.

Because Oakleigh Football Club made no effort to co-operate, the new Committee passed a motion to never wear the purple and gold of the Oakleigh VFA. The Districts have long memories. In 1994-95 after the VFA restructure, and Oakleigh VFA went into recess, there was some discussion about the Districts taking on the defunct Oakleigh VFA guernsey. Those discussing the possibility were reminded of the motion, some 44 years earlier, and the discussion duly ceased. 

Former St Kilda backman Stan Le Lievre was appointed the Districts inaugural coach for 1950 at four pounds per week. Apart from his playing ability, Stan was also famous for his Plymouth ute, which often seen on match days carrying more than the legal allowance. Whoever could not fit in, hung over the sides. "One day I had 17 blokes in that ute" said Stan some years later. The reason that Stan’s ute was so popular, was that in the entire Club, apart from bicycles, the only other modes of transport were one other old ute, and two even older motor bikes.


Prior to the formation of the Districts, the only other open age side in the Oakleigh area, apart from Oakleigh VFA was Oakleigh United, however they had disbanded after the 1949 season.  Remarkably, they had left 50 pounds in trust to any other Club that could start up an open age side, within the City of Oakleigh. The Districts were successful in meeting the criteria for a new startup Club, and so gained the opportunity to use the 50 pounds. This money went a very along way to getting the Districts started.

The first home ground was the ‘Police Paddocks’ – along the Dandenong Road Broadway, to Park Road, and down next to Scotchmans Creek, where the Oakleigh Swimming pool and Sporting complex are now situated. The area was named the Police Paddocks because it was the area where the local police horses were agisted in the late 1800’s. The area was not that attractive. It was away from Oakleigh’s central residential and shopping areas, and somewhat logistically removed from the usual activities of an Oakleigh day.

The original ‘change room’ ( if you could call it that ) was a tin shed approx. 5 mtrs by 4 mtrs, with a leaky tin roof, an unlock-able battered wooden door, and a lean-to small veranda with a broken and hole-ridden timber floor. The tin walls were full of holes, there was no internal lining or plaster, old coir cricket mats were hung to help keep the wind out.


No hot water, light or electricity, and the one cold water shower recess (with no showerhead)  was usually full of broken glass from vandals activities during the week. After a game and at training, one of the players Jack Peake would occasionally drive his motorbike through the doorway and put the headlight on, to light up the room.  There was no canteen, and the visiting opposition sides would change in a furniture van that would bring their players and supporters to the game. It was Spartan, at best.  

At the East end of the ground was the Oakleigh Brickworks quarry which was very deep at approx.30-40 meters. Most times when a game was being played, a solid kick through the goals would see the football sail over the brickwork's fence, and into the bottom of the quarry. Luckily the Club had Committee members who worked in the quarry and they would retrieve those lost footballs on Monday morning. The Districts like most Clubs of the day only had 5-6 footballs for the whole Season. Footballs were an expensive outlay for all Clubs. 

The scoreboard, which was a timber framed construction, with white numbers painted on black square metal plates, which during the games, were then hung on nails, was situated on the south-east flank, and built by Stan Peake, who did a lot of early work around the Club. The Peake family were to become a generational institution for decades at the Oakleigh District Football Club.

The actual ground itself was in a parlous state, to say the least. It was small, narrow, uneven, and unfenced, with a noticeable camber down to the Southern (Marriott Street) wing.  Some parts of the surface, were downright dangerous, with ankle and knee injuries not being uncommon, particularly for visiting teams. During the drier months, it was rock hard clay and sparsely grassed, and the red ‘Mercurochrome’ antiseptic was a standard requirement by those helpers on the day, and very freely used as bloody skin grazes were common. (Bill Ruffles was the original ‘Trainer”).

In the wetter months it was an ankle-deep quagmire. Those visiting (who had vehicles) slowly idled around the pot-hole puddles that riddled the boggy track, that partially surrounded the ground, to the ‘change-room’. The ground never had a floodlight for after work training, so not many football drills could be often practiced. Many cold winter nights were spent just running laps, and doing Indian file, in the pitch-black dark, but the unwavering camaraderie between the players was forged, during those hard times spent together.  Few sides, if any, ever liked visiting and playing the Districts at the ‘Police Paddocks’, as not only were the conditions hard, but the games, weren’t too easy either.

The original Players List – 1950.
R Anderson  H Ashton B Atkins
G Barnfather  A Bell  R Brewster  J Bruce  P Burns  
E Camm  K Cook  B Cunningham
D Baird  B Dowd  M Doveston
N Eden.
R Follett
F Kight A Knights.
B Lever I LeGriffin S LeLieve
J McConnell
A North
J Peake
G O’Mahony
R Rees  P Richardson W Robertson
B Sambell
R Tait  J Tierney
W Wilson
W Podesta
                                      
The first Oakleigh District Home game was against
Murrumbeena on the 22nd April 1950. 
Murrumbeena 23-19-157 d Oakleigh Dist 5-17-47.

First win was on the 1st July 1950.
Scores: Oak Dist: 15-10-100 d East Brighton 8-9-57

SNIPPETS from The Districts first ever win
Saturday 1st July 1950.
 “Oakleigh Districts in Brilliant Win”
Oakleigh Districts overwhelmed East Brighton at the Oakleigh ground with fast systematic football. Stan LeLievre, the Capitan and Coach of Oakleigh Districts shadowed Brighton champion full forward Harry (Soapy) Vallence past VFL and Association star.  Stan’s long driving kicks, high marks, and spoiling tactics were a delight to watch, and Vallence was nullified for most of the day. The Oakleigh District centre line of Kight (best on ground) Anderson, and Atkins was a match winning factor frequently kicking their team into attack.
Best Oak Dist Players: F KIGHT, S LELIEVRE, B ANDERSON, B ATKINS, R REES,
H ASHTON, B CUNNINGHAM, G BARNFATHER.

The second win was the next week on the 8th July 1950
Oakleigh Districts defeated Caulfield.

The Third win was on the 12th August 1950. 
Scores: Oakleigh Dist 14-14-98 d East Malvern 7-7-49
Oakleigh Districts finished ninth which over all was
a good result for the first year.

The inaugural Best and Fairest winner was Bobby Anderson (known as ‘Kanga’ because of his prodigious leap) who went on to play a then record 147 Senior games plus at least that many again, in the Seconds. He also coached many Oakleigh District under-age junior sides for many seasons.  The first Trip Away was to Geelong.