The first part of the 1940/41 season saw the ANA First Eleven's struggling form continue. The war was having a definite effect on the competition, however, but ANA was not affected as badly as most other clubs and the second half of the season saw them come home with a "wet sail" and finish off in the final four, in only a six team competition. Facing the old foe and top team, the Bentleigh Footballers, in the Semi-final, ANA continued its good form and won comfortably. This was due mainly to the efforts of Alan Gray with 65 and 34, Wally Munro with 42, Wally Comber taking 6/10 and the consistent finals performer Ern Bulte in making 41. Alan Gray then virtually played a lone hand in the Grand Final against West Bentleigh, when he made 39 not out and 49, but his efforts were not enough and ANA went down easily in yet another Grand Final loss. Throughout these early years, and for many years to come, the members of the Bentleigh ANA Cricket Club used the ANA (Australian Native Association) rooms situated above the old Bentleigh Picture Theatre in Centre Road as the base for all of their meetings.

The team remained fairly stable throughout this season, and with the added experience of the year before, resulted in the combination being a stronger one. Now boasting the Association's batting average winner, Stan Barras, who had been recruited from Highett, ANA was once again able to sneak into the "four". In the Semi-final, the ANA team avenged last season's defeat by West Bentleigh, as Ern Bulte with 46 and Alan Gray with 36, set up the scene for ex-Highett spinner Joe Donavon to return match figures of 9/34 and bowl ANA into another Grand Final. ANA once again came up against none other than the Bentleigh Footballers and set about the task at hand confidently. Captain and wicket-keeper George Grove led the team by example with a hard hit 31 while the experienced Ern Bulte once again slammed up a personal best, with an unbeaten 68, as ANA struggled to a total of 179 in the first innings. Speedster Wally Comber then bowled superbly to take 5/36 as ANA grabbed a small first innings lead of 19 runs. But again, as had been seen so often before, the "wobbles" set in and ANA could only manage a meagre 68 runs in the second dig. In an attempt to save the seemingly lost Premiership, Alan Gray bowled valiantly at the Footballers in their second innings, taking 4/37, but in a nail-biter, ANA went down by just two wickets as the Footballers clawed their way to a Premiership winning score of 8 for 89. In an amazing era ANA had now appeared in no less than seven Grand Finals, for just the single Premiership. It was also during this period the Club was saddened to learn of the death of player Norm O’Hare, while serving in the war. He was in his third year with the Club when called upon to serve his country and, as a result, paid the ultimate price.

Alan Gray was to take over the captaincy for the 1942/43 season as George Grove had returned to Highett. However, the loss of Grove was compensated for by the recruiting of Len Grewar, Les Bowen and Harry Edwards, who were all from the Bentleigh Free Gardeners Cricket Club, which had recently disbanded due to the War. Also, the inclusion of Clem Conroy, off-spinner Charlie Hockley and 16-year-old Ken Haw made this team a very strong one. Tragedy again struck the Club mid-season when Alan Gray's brother, and regular 'A' Grade player, Roy Gray, drowned while taking a lunch-time swim at a local pool. Once again the Club had lost a fine team member. The weakened competition allowed the young ANA team to sneak into the finals series, facing the might of the Bentleigh Footballers in the Semi-final. In a low scoring affair, Charlie Hockley spun ANA to a small first innings lead with a magnificent 8/20. Needing to make only 105 runs to win, ANA struggled enormously and only the single-handed effort of Joe Donavon with 47 not out, allowed them to steal a victory by two wickets. ANA faced the much improved MUIOOF team in the final and thanks to a punishing hand of 94 from the hard hitting Harry Edwards, were able to set their opponents a respectable 179 in the first innings. Wally Comber with 7/30 and Charlie Hockley with 6/38, then set about destroying the successive innings of MUIOOF, enabling ANA to cruise to their second 'A' Grade Premiership. This was an exceptional effort from Alan Gray, who had led the Club to a Premiership in his first year as Captain. Also this season, the evergreen Harry Robinson led the Second Eleven into the finals for the first time. ANA batted first against the GUOOF team and John Dennehy offered the only resistance hitting up 35 out of a miserable total of only 107. As if this wasn’t enough, Dennehy then bowled with venom to capture 5/28 but the GUOOF’s had struggled to a seven run lead on the first innings. With quick runs now being the order of the day, Alan Wilson led the charge with 74 and he received fine support from Doug Coates, who finished unbeaten on 38, as ANA reproduced the form that had been so impressive throughout the year, to make 166 in the second innings. Still requiring to dismiss the GUOOF's again for victory, John Dennehy again led a team which refused to accept defeat and in the second innings he finished off his fine Semi-final performance by taking 4/6 as ANA bundled out the GUOOF's for a meagre 63 runs. Sticking with the ploy of batting first, Robinson once again elected to put the pads on first in the Grand Final against the Ramblers Cricket Club. Luckily for ANA, Ron Jones was in excellent touch as he produced a memorable innings of 88 while wickets collapsed around him, and when he was dismissed, ANA had been bowled out for a modest total of 144. Again it was up to the bowlers to swing the game in ANA's favour and it was Dennehy and Coates who completed this task. Dennehy continued an excellent finals series by taking 4/26 while Coates bowled with great control to snare 3/33 as ANA routed the Ramblers for only 86 runs. Now in a commanding position, the ANA batsmen had the opportunity to put the match beyond doubt but as was the case in the first innings, most failed miserably. Only for Jones hitting up a defiant 37 and some hard hitting by Dennehy in the lower order, as he and Alf Belton added 38 for the last wicket, ANA would not have reached their final score of 102 in the crucial second innings. Requiring only 160 for victory the Ramblers viewed their chances optimistically, but the ANA bowlers were again as determined as ever. Ron Jones capped off a memorable Grand Final by taking 3/12 and skipper "Long Robby" Robinson appropriately captured the last three wickets to take 3/10 and lead the 'B' Grade to its first

Premiership as the Ramblers crashed to be all out for 58. In doing so, ANA became the first club to win both the 'A' and 'B' Grade Premierships in the same season and had now secured itself as the strongest club in the competition.

Leading ANA Lodge executive member, and keen cricket enthusiast, Alan Ellis Snr. took over the Presidency for the 1943/44 season from Bentleigh jeweller Percy Jack and the ANA Seconds were relocated to their new home ground at the McKinnon Reserve in Tucker Road. The competition for this season comprised of an unusual format. Up until Round 7 there was only one grade. At this point only the top five teams remained in 'A' Grade with the remainder forming a 'B' Grade. ANA fielded two teams once again, with the Firsts finishing in the top five. However, this young team could not reproduce their feats of the previous Premiership year, and even with Wally Comber and Alan Gray capturing 40 wickets each, the team failed to win a place in the "Grand-Final-only" play-off for the Premiership.

The disbanding of the West Bentleigh club for the season 1944/45 saw the St.Kilda Footballer, and cricketing all-rounder, Col Williamson join the Club along with veteran all-rounder Les Coulson. Combining this with the inclusion of the fine allrounder Bill Kett and batsman/wicketkeeper Alan Bonnett, much needed strength was added to the Senior team. This resultingly strengthened the 'B' Grade team also. Harry Edwards had developed into one of the best hard hitters in the competition, amassing over 400 runs for the year, and ANA lost only two games, both narrowly, before entering the final’s series. The Semi-final was another ANA versus Footballers confrontation which saw ANA emerge victors in a closely fought battle, due mainly to the fighting innings of 31 and 38 by Phil Hobbs and Alan Gray respectively. This set up a Grand Final battle against the Brighton Union team, who were attempting to win their first Premiership in the recently renamed City of Moorabbin Cricket Association (CMCA). Led once again by Alan Gray, the strong ANA team could only manage 136 runs in their first innings. Not to be denied, however, Alan Gray with 4/20 and Col Williamson 5/19 then set about destroying the Brighton Union first innings, allowing them only a paltry 49 runs and seemingly assuring ANA of a third Premiership. The Union team did not accept defeat easily, however, and fought hard to dismiss the ANA team for 106, giving ANA a 193 run lead overall. Seeming almost certainties for the flag, the ANA bowlers were then awe-struck as the Union batsman hammered the ball to all parts of the field and somehow, amazingly, managed to steal the Premiership and forge to victory by three wickets. It was one of the biggest fight-backs ever to be seen in a CMCA final and once again it was the luckless ANA that had endured the raw end of the deal. Bob Butters with 35 and Ken Haw with a fine 48 had led the 'B' Grade team into the Grand Final, after a Semi-final win over the Deutschers Cricket Club. Alas, ANA found that they were no match for the strong Brighton Union Second Eleven and also had to be satisfied with being Runners-Up.

The end of World War II, saw the re-formation of several clubs and the resultant departures of Col Williamson and Les Coulson from ANA. Local Bentleigh identity, George Hyde, joined the Club for the 1945/46 season, playing his first cricket since being locked up in a German Prisoner Of War camp for over five years. However, George's ongoing celebration of his return to civilization tended to rather badly influence his on-field performances and he failed to reproduce the cricket which made him a fine cricketer with the Bentleigh Gardeners before the war. ANA's bowling line-up, consisting of Alan Gray, Bill Kett and Doug Coates, provided sufficient strength to lift the team into the finals once again. However, only Phil Hobbs with 24 and 32 and Alan Gray with 5/63 offered any resistance to the Footballers in the Semi-final and the team was soundly beaten.

In season 1946/47 the ANA team was greatly strengthened by the recruiting of Col Turner, a brother-in-law of 'A' Grade stalwart Lenny Grewar. Turner, a right-arm fast bowler and hard hitting top order batsman, had played District Cricket in Queensland while serving in the war. Bentleigh veteran Bill Ogden also returned to ANA this season to play out his cricketing years with the Club. ANA seemed certain for success this year. Alan Gray again led the Club throughout the season, but informed the Club mid-season, that he would be unavailable for the Grand Final, due to the fact that he was going to Sydney to live after accepting a business promotion. Because of this, the rest of the players took a vote mid-season and elected Ken Haw as Captain for the remainder of the year, in a decision that was to cause some controversy. This 'A' Grade team had an inconsistent year and only just managed to sneak into the final four. The brilliant Turner made 52 and returned match figures of 10/36 as he destroyed West Bentleigh in the Semi-final, receiving support from Bill Kett who finished with match figures of 6/39.

Thus another Grand Final show down with the Bentleigh Footballers. Weakened by the absence of opening bowler Alan Gray, ANA struggled to eventually dismiss the Footballers for a daunting total of 263, with Col Turner taking 6/109 and Bill Ogden 3/11. ANA then chased the score gallantly, with Bill Kett leading the runs with 70 and obtaining support from Turner with 32 and Ken Haw 27, as ANA got to within 80 runs of the Footballers' total. Turner with 4/37 and Ogden with 3/34 then gave ANA a chance of victory as the Footballers were dismissed for 141 in their second innings. However, the 220 runs required proved too great a target as ANA crashed to be all out for 73 in their second innings. Kett

making 24 and being the only batsman to offer any resistance.

Desperate for another flag, ANA promoted Cliff Colk back into the 'A' Grade after he had played in the 'B' Grade for several seasons. Also, former Bentleigh Gardener's batsman Jack Lees, turned out for ANA and the Club was confident of a good season once again. In a somewhat amusing situation, after having shown mediocre form in the 'A' Grade, ANA wished to drop newcomer Jack Philipson to the 'B' Grade. But as rules then stood, they were obliged to apply to the CMCA for permission to do so. Following much discussion and debate, ANA was finally given permission to demote the tall all-rounder, only to see him make a mockery of the decision by taking 6 for 0 in the very next game. Throughout the season Ken Haw led a strong bowling line-up of Col Turner, Bill Kett and Cliff Colk. Turner had been sensational, bundling out no less than 62 batsmen for the season. But the batting performances of the team did not give the bowlers adequate support and ANA went into the finals series very much an out of form team. Once again the Bentleigh Footballers showed no mercy in this Semi-final game, with their feared batsman Jack Dunlea, blasting his way to a double century. Ken Haw's 4/72 and Len Grewar's 71 were the only bright patches in a game which saw ANA fail to make an impression and eventually being defeated outright by an innings and 32 runs.

Season 1948/49 was highlighted by the event of ANA fielding two teams in the 'A' Grade competition. They met each other in Round 6, the round during which Herb Simmons crossed over to the Club from the Bentleigh Footballers. In this game, Simmons played for the Second Eleven, led by Jack Philipson, and provided a few scares for the First Eleven team, when he helped himself to a fine score of 95. The ANA No. 1 team eventually managed to win the game and Herb was rather smartly promoted to the First Eleven for the remainder of the season. Ken Haw was the Captain of the First Eleven team, but dropped himself to the Seconds mid-season and Alan Bonnett took over the job. The ANA No. 1 team went through the season undefeated, a feat that still remains to be the only time that the ANA First Eleven has done this. The ANA No. 2 team narrowly missed the finals, finishing in fifth place. Considering the ANA No. 1 team had pounded a massive 433 against the Bentleigh Methodists only one month earlier, they went into the Semi-final against the Meths full of confidence. As had been the case throughout the year, Col Turner was in sensational form in the Semi as he made 51 runs and took 5/42 and 6/51. This had initially set ANA up with a 20 run first innings lead and then consolidating the situation as ANA were left with a target of only 87 runs for a second innings victory. Disaster then struck, however, as the Green and Gold crashed to be all out for a miserable 58 runs. Once again that elusive Premiership flag had eluded them. Amazingly, in the first nineteen years of competition, the ANA 'A' Grade team had appeared in no less than fourteen final's series, for just two Premierships.

Season 1949/50 saw the emergence of shrewd administrator and hard worker Jack Philipson as Secretary. He wasted no time at all in making his presence felt and at the age of 30, and after a 13 year absence from the Club, Cyril Parke was enticed back out of retirement. Also, Jack had a large influence in the introduction of an "Under 16" team at the Club, but sadly this team lasted for only two seasons. In these financially tough times, players tended to become more attacking as the afternoon went on, often enabling a result to be obtained well before the scheduled 5:30 finishing time each Saturday. Having achieved this, Messrs Haw, Bonnett, Edwards, Turner and Co. would often make a beeline for the local Boundary Hotel, allowing ample time for several "amber" refreshments to be consumed before the regulation six o'clock closing. On days where an exceptional thirst had been developed, a "gallon-jar" would be filled with "take-aways", and once packed in ice and returned to the ground, this would serve as adequate means to keep the beer cold for enough time to satisfy the thirsty team. Tall all-rounder Bill Johnson arrived at the Club to replace Bill Kett, who had left for Ringwood, and youngsters Bruce Smith and Ralph Sturt made their debuts throughout the season. Herb Simmons was elected as Captain and the prospects of the team looked good, considering their fine form of the previous year. However, Col Turner and Harry Edwards were to both miss the first half of the season and only when they did return, did the team begin to find some consistency again. Evergreens Bill Ogden with 42 wickets and Cyril Parke with 400 runs both had a big say in seeing ANA sneak into fourth position at the end of the Home and Away matches. However, the finals series saw the ANA team at its strongest and a fine all-round effort by all batsmen and bowlers saw them defeat the Ramblers quite comfortably in the Semi-final. Alas, it was once again the Bentleigh Footballers who faced ANA in the Grand Final. Controversy still surrounds the selection of the team, as the failure to take a wicket in the last two matches saw 15-year-old spinner, Bruce Smith, dropped after having played the entire season in the 'A' Grade. In this final, however, Skipper Herb Simmons led by example with a fighting knock of 92 and he was well supported by Harry Edwards with 48 and Bill Johnson with 42, as ANA amassed an excellent total of 273. Edwards then put an end to any chances that the Footballers might have had by taking six wickets in the second innings, giving ANA outright victory by an innings and 32 runs. Herb Simmons had the rare distinction of being successful in leading ANA to their third 'A' Grade Premiership in his first, and what was to end up being his only, year as Captain.