He was the champion of the previous year's Clubsplosion tournament and returned to defend his title with his Throh. He has shown a particular interest in Stephan and his Sawk. However when Stephan began bragging that Sawk was the greatest, he took slight offense to it. He stated that Stephan could not say he was the greatest until he won a battle against his Throh. Even then, he had concluded that Stephan would not make it past the second round just by looking at Sawk.
Still, Montgomery continued to observe Stephan and Sawk in Search for the Clubultimate! during the intermission while they were attempting to help Ash's Scraggy direct his Focus Blast. Afterwards, Montgomery fought his first opponent, Delbert, and defeated him easily, and advanced to the second round.The night before the second round was to begin in A Clubsplosion of Excitement!, Montgomery was seen training Throh by having him throw large boulders around. Ash asked him to train with him and Stephan but he refused; saying that he did not train with his "enemies". The next day he went up against Iris and her Excadrill and won, advancing himself to the semi-finals. Before the episode's conclusion it was revealed that his opponent for that round would be Ash and he battle him in Commanding the Clubsplosion Crown!. Montgomery was well aware of how badly Scraggy aimed his Focus Blast attacks and did not issue a command to Throh. Instead they waited as all of his Focus Blasts missed. He finally told Throh to attack after Scraggy used Hi Jump Kick and things went smoothly for them afterwards. Ash was yet another defeated opponent soon and Montgomery would join Stephan in the final round of the Clubsplosion.
Stephan would prove to be his toughest opponent yet to the point where Montgomery struggled to maintain control of the battle. However, he eventually lost and was forced to give up his championship title. Though he did lose, he was thoroughly impressed by Stephan's skills as a Trainer and congratulated him when he won, even giving him a handshake. He did say that the next time he and Stephan battled, he would be victorious.