The old style of tournaments were over and if there were to be a Fourteenth Tournament a few gambles would have to be taken. It would only be a matter of time for the tedium of predictability to rear its ugly head again, so it was decided to once again expand to two divisions. Lieutenant Gareth made his return to Division Two, a competition he had won at the Tenth Tournament and Earl Holbrook was invited to join the Fourteenth Mega Drive Championship. There were changes in the game pools that would be used in both divisions. It was decided that ten games would be in each pool with five games used in both divisions and five exclusive to each league. For the first time in tournament history games were tested to see whether they would be suitable for the competition. With the exception of Road Rash 2, all the games used in the Thirteenth Tournament carried on for use in Division One. Ball Jacks, NHL '96 and Streets of Rage 3 were also included in the line-up. The Division Two games used at the Tenth Tournament re-appeared with the omissions of Pete Sampras Tennis (which was to be used in Division One) and NBA Jam. Ball Jacks, NHL '96 and WWF Super Wrestlemania were added to the Division Two game pool. Meanwhile the struggle to find members was reaping few rewards and so it was decided that Captain Maltby, who finished bottom at the Thirteenth Tournament, would be relegated to Division Two.

The most important change to occur in the break between the Thirteenth and Fourteenth Mega Drive Championships was the emergence of the Tournament Administration, as the body that made all decisions regarding the Mega Drive Championships. During early tournaments any decision put forward needed the approval of all members in order for it to take effect. Because of this there were no notable changes to the tournament structure until the Seventh Championship, and even then only the threat of complete capitulation of the competitions forced alterations. It was not until the setting up of Division Two at the Ninth Tournament that the balance of power changed. Decisions were required and the old style was ineffective for both introducing and approving changes, but the biggest problem with a unilateral agreement was that, as the tournaments grew, the odds of everybody agreeing became remote. A more democratic style would have suited a large number of peoples, but it was also feared that the new Division Two members might vote in a motion that would be detrimental to the Mega Drive Championships. An idea to give a democratic decision making process to Division One members took a step towards the eventual solution, but it was ultimately rejected for fear that eventually the four current members could lose all influence over their creation. Eventually the concept of the three "founding fathers" (Doc Shakib, Lord Dilks and Mr Smith) making all tournamental decisions emerged. The process contained too much internal politicking and bickering over trivial issues to ever be successful, as each "father" attempted to gain the support of one of the others in order to have a decision ratified. In the build up to the Fourteenth Mega Drive Championship, Lord Dilks and Mr Smith voted Doc Shakib from power. Without the pettiness of democracy hampering progress, the new Tournament Administration was able to focus on implementing the changes required to make the Fourteenth Mega Drive Championship "better than the other Thirteen combined" and to that end they were successful.

There were a few final alterations before the Fourteenth Mega Drive Championship. Dame Yada became the first non-UK resident to enter the tournaments and she took her place in Division Two alongside Captain Maltby, Earl Holbrook and Lieutenant Gareth. There was a final change to the Division Two games with European Club Soccer being replaced in favour of FIFA Road to World Cup '98. One of the biggest decisions by the Administration leading up to the Fourteenth Tournament was the huge financial gamble of including real trophies. The First Tournament had nothing and the winner, Mr Smith, had to be contented with the knowledge of his victory. A small trophy was given to the winner of the Second Tournament, Lord Dilks, and it was then passed around the winners. Similarly the Tournament Knockout never had any prize, although the idea of a plate/vase was discussed on more than one occasion. Other than the cost of trophies it was feared that their presence would add a seriousness edge to what has always been a light hearted competition, that it would be seen as arrogance on the part of Lord Dilks and Mr Smith and if the tournaments collapsed there would be a small collection of redundant trophies. In the end, the an array of silverware was added and was to be awarded to the Mega Drive Champion, Knockout winner, Division Two winner. The Street Fighter Challenge was also revamped, with an Eternal Champions section added for the Division Two members with the winners of both competitions going head-to-head in a final game of Super Street Fighter 2, both the finalists received trophies.

Despite the unfamiliar surroundings it did not take long for the Fourteenth Mega Drive Championship to get into its full swing. The new trophies, new games, new members, a buffet and an almost endless stream of coffee marked the latest evolution of the competitions. Just four-and-a-half years earlier it had been three college students holding a competition during their free periods to see which one of them would be Mega Drive Champion. Unlike the previous tournaments the league was once again central to the event and it was carried onwards by the lighthearted atmosphere that had survived from the Thirteenth Tournament. Lord Dilks won the Fourteenth Mega Drive Championship after accelerating into an early lead over Mr Smith who ended up five-points behind him in second. The relegation scrap, in Division One, was contested between Baron Von Hooton and Doc Shakib. This scrap was effectively over after the penultimate game where Baron Von Hooton drew 4-4 with Mr Smith on NHL '96 and pushed himself one point ahead of Doc Shakib. Although Doc Shakib fought on against Lord Dilks on Pete Sampras Tennis, it was a game that was almost impossible to win and he was relegated for the second time in his tournament history. Mr Smith won the Tournament Knockout following a close encounter against Lieutenant Gareth on Super Street Fighter 2. Mr Smith was the only Division One member to make it into the semi-finals, with Baron Von Hooton, Doc Shakib and Lord Dilks all knocked-out in Round One. Lord Dilks won the first Challenge Trophy where he beat Dame Yada 2-0.

If one problem persisted it was that of members. By promoting both Captain Maltby and Lieutenant Gareth to Division One, the lower league needed an infusion of fresh blood so that there was not a huge inequality in the sizes of the league. This problem was quickly aggravated when Dame Yada was denied an extended UK Visa and had to return to America. By January 2006 Division Two consisted of Doc Shakib and Earl Holbrook. Over the next few months the Tournament Administration embarked upon a frantic quest to swell tournament numbers. During this period many names emerged only to quickly disappear. Viscount Player became the first new member to join the Second Division and Commander Graham quickly followed him, with both the pair expected to challenge Doc Shakib for the Division Two title. Meanwhile Sir Ewings was hauled on board in order to become the fifth member in the lower league, however, he quickly disappeared having never even picked up the controller. Viscount Player was another one who, due to circumstances, was unable to participate in the competition and once more things were looking bleak.

But things were progressing quickly, although the tournaments had largely been ignored for the remainder of 2005, the first six-months of 2006 flew past. The biggest change to the system was a third place match being added to the Challenge Trophy. Meanwhile there were a few changes made to the game pools. Golden Axe 2 was replaced in the lower division with Alien Storm while NHL '96 was taken from Division One. Columns was added to both divisions while FIFA Road to World Cup '98 was replaced with Sensible Soccer. WWF Super Wrestlemania was axed from the Second Division, as it's original intention was to be that of an enjoyable, not-to-serious, unskilful scrap - it failed to live up to its expectations. Road Rash 2 was also replaced by its sequel game, Road Rash 3.

Old Spice Lock became the latest person to pledge himself to the Fifteenth Tournament. This upped the total number of Division Two members to four and with little over a month to go, King Stansfield agreed to join the event. Up until this point it had seemed likely that Captain Maltby would be denied promotion in order to balance the two leagues. Fortunately this never occurred. With just a few weeks remaining before the Fifteenth Mega Drive Championship, Chaplain Womersley emerged as the sixth tournament member to be added to Division Two. Yet, on the day of the tournament, King Stansfield did a disappearing act and, like Sir Ewings before him, has not been heard of since. With five members remaining in Division Two the entire competition was able to continue without interruption or panic.

After another short delay due to technical problems with the game recordings, the Fifteenth Mega Drive Championship kicked off just before 7pm on the 11th July 2007. The Challenge Trophy was the first competition contested. The relegation scrap in Division One was the most exciting, taking many twists and turns with Baron Von Hooton, Captain Maltby, Lieutenant Gareth and Lord Dilks all spending time in fifth place. Lord Dilks lost his first two games and found himself at the foot of the table, however, his form improved and he pulled himself into the top half of the table leaving Baron Von Hooton, Captain Maltby and Lieutenant Gareth to fight it out between them. The outcome of the relegation battle was not decided until the final game. A win on Streets of Rage 3, against Mr Smith, had secured Lieutenant Gareth in third place and left Baron Von Hooton and Captain Maltby the only two who could drop down to Division Two. Ironically the final game was Baron Von Hooton versus Captain Maltby on Ball Jacks. Baron Von Hooton had never been out of the top league while Captain Maltby had been the favourite to return to Division Two, but with the final claxon it was Captain Maltby who was victorious with a convincing 3-0 victory. Captain Maltby also popped up as the surprise winner of the Tournament Knockout. He beat Mr Smith, Doc Shakib and Baron Von Hooton in his journey to pick up the Knockout Shield. Mr Smith won his eighth Mega Drive Championship following a 2-0 victory over Captain Maltby on Super Street Fighter 2. Lord Dilks ended up in second place having recovered from his poor start while Lieutenant Gareth secured his highest league finish, third place. In Division Two, Doc Shakib was light years ahead of the competition and won a return to the top division with seven wins and one draw from eight games - the best Division Two record to date. Commander Graham finished in second place.

A decision was made in October 2006 that there should be a winter tournament in 2007. While summer tournaments came as standard, there had not been a Mega Drive Championship in winter since the Thirteenth Tournament. The Sixteenth Mega Drive Championship marked the end of a long era, as it was the final tournament for both Baron Von Hooton and Mr Smith. Baron Von Hooton spent his final tournament in Division Two, while Mr Smith opted not to participate in the league and instead played his final three games in the Tournament Knockout. Division One was a tightly contested affair with Doc Shakib and Lord Dilks vying for the title and Captain Maltby and Lieutenant Gareth slugging it out to retain their place in the top league. Yet Division Two was the most interesting competition with four of the five members still mathematically able to earn promotion at the three-quarter-way point. Ultimately it was Commander Graham who won promotion to Division One, winning by just a single point when Baron Von Hooton lost to Professor King on Streets of Rage 2. The inaugural Division Two Cup was also an interesting event with the final seeing Baron Von Hooton beat Professor King on Sonic the Hedgehog 2. Sonic the Hedgehog 2 was the game which decided the Division One title and relegation, Doc Shakib's victory over Lieutenant Gareth not only secured Doc Shakib his first title since the Seventh Mega Drive Championship, but also condemned Lieutenant Gareth to the Second Division. Mr Smith won the Tournament Knockout after a victory against Lord Dilks in the Golden Axe 2 final.