At the turn of the 20th century, Glebe was a working-class suburb of Sydney, situated a few kilometres to the west of the city centre. The club began their premiership campaign with an 8–5 victory over
Newcastle on 20 April 1908. Throughout the season they either remained close to or on top of the ladder and with one round remaining were on equal points with
South Sydney and
Eastern Suburbs to lead the competition. In the last regular-season match, Glebe went down 10–5 to sixth-placed
Balmain and ended up running third overall, although the match ended up having no impact on who they would play in the finals a week later. In their semi final, Glebe went down 16–3 to
minor premiers South Sydney and were knocked out of the competition. In 1910, the club had a mediocre season and had little chance of ever taking the premiership out. The 1911 season was arguably the most successful in the club's history, taking out the minor premiership outright by two points and winning 11 of their 14 matches on the way. They also secured their first-ever victory over local rivals Balmain, winning 41–2 in the second last regular-season match of the season. However, they came up against an Eastern Suburbs side led by
Dally Messenger who had won six matches straight. After 10 rounds, Glebe trailed Eastern Suburbs by just two points and were to face them the following week with four rounds to go. In a match in which Glebe almost certainly had to win to stay in premiership contention, Eastern Suburbs won a close match 6–4 in front of another record crowd of 25,000 at the
Sydney Sports Ground and ended up taking away the premiership four points in front of Glebe at the end of the season. In 1915, however, they came close to taking out the premiership. With four rounds remaining and equal with their local rivals, Glebe were to face the undefeated Balmain at the Sydney Sports Ground. Again, however, Glebe failed to win this crucial game, losing 12–2 in front of 20,000 people and allowed Balmain to take a one-match lead. With both teams winning their remaining games, Balmain ended up taking out the premiership. Overall in 1915, Glebe won 12 out of their 14 matches, a club best, losing twice to Balmain. In 1917, Glebe was involved in a dispute with
Annandale for fielding a player that did not reside in Glebe's district. As a result, former Newcastle player Dan Davies received a life ban from all rugby league. The entire Glebe 1st grade squad disagreed and went on strike. All Glebe 1st grade players were suspended. Three of the Burge brothers, including
Frank Burge, were banned till the start of the 1919 season (an eighteen-month suspension), however many of these suspensions were subsequently overturned or shortened. Further implications came into the Newcastle Rugby League, where the competition was split until 1920. Glebe finished out the decade continuing to win more games than they lost each season and regularly finished within the top four, but without a finals system in place they were unable to capitalise on this relatively strong position. In 1922, they finally gained another shot at the premiership when they and
North Sydney finished on equal points at the end of the season. In the ensuing final, North Sydney easily accounted for Glebe 35–3, again denying Glebe the elusive premiership title. From 1923 onwards, the club's form started to decline and for the first time since 1910, Glebe lost more games than they won. In 1926, they were given another shot at the premiership when the finals series was reinstated. Finishing second to runaway leaders South Sydney, Glebe were to face off against fourth-placed
University for a place in the final. However, they lost this decisive match 29–3 and were sent out of the finals. In their final three seasons, Glebe struggled at the bottom of the premiership after the departure of their long-time player
Frank Burge. Out of nine teams they finished eighth in 1927, seventh in 1928 and eighth in 1929. However, others suggest that the local area was changing in such a way that the club was probably on a road to its demise anyway.
2018 On 5 January 2018, it was announced that Glebe would be returning to play preseason games at
Wentworth Park which would be the first time that rugby league has been played there in 90 years. The matches also featured the
Newtown Jets and the
Blacktown Workers Sea Eagles. For the 2018
Ron Massey Cup season, The
Concord-Burwood-Glebe Wolves changed their name to the Glebe-Burwood Wolves. On 11 February, Glebe played alongside fellow foundation club Newtown at
Wentworth Park in two pre-season trial matches. It was the first time in 90 years that a professional game of rugby league had been played at the ground.
2019 On 17 February Glebe returned to
Wentworth Park and played in a pre-season trial against
North Sydney which finished with Glebe running out winners 24–12. This was the first time Glebe had played against North Sydney in 90 years with their last meeting being in 1929. At the end of the 2019
Ron Massey Cup season, Glebe finished in second last position on the table only 2 points above last placed
Brothers Penrith.
2020 On 16 February, Glebe played in a pre-season trial match against fellow foundation side
Newtown at
Wentworth Park. It was the first time in 91 years that the two clubs had played against each other in a game. Newtown would run out comfortable 20–0 winners. Due to the COVID-19 pandemic. The
Ron Massey Cup and
Sydney Shield competitions were cancelled along with the
Canterbury Cup NSW. As a result, Glebe entered into the temporary
Presidents Cup competition. Glebe would go on to reach the grand final against the
Maitland Pickers but were defeated 17–16 at
Bankwest Stadium.
2021 For the second year running, the
Ron Massey Cup competition, along with all
NSWRL competitions, were halted due to the COVID-19 Pandemic, and were subsequently, cancelled.
2022 In the 2022
Ron Massey Cup season, Glebe reached the grand final against
Hills District but were defeated 18–12 at
Kogarah Oval.
2023 In 2023, Glebe formed a partnership with the
Sydney Roosters, ending a five-year partnership with
Newtown. Glebe also introduced a
Sydney Shield team, and will be playing all their home games from Wentworth Park in Glebe, alongside the Sydney Roosters
Knock-On Effect NSW Cup and
Jersey Flegg teams.
2024 On 14 September, Glebe won their first Ron Massey Cup title defeating
Wentworthville 19–6 in the grand final which was played at
Leichhardt Oval. == Seasons ==