In late 1938 at the league's winter meeting, Mr. Ben Howard of Union City was elected president of the league. Howard had two years experience as the leagues vice president and several years working with the Union City franchise. Shelby Peace was re-elected vice president to Howard.

A seven and one-half hour meeting was held in Paducah's Irvin Cobb Hotel on January 23, 1939. There was discussion over raising the number of scheduled games to either 132 or 140. When the league finally began play it had settled on a 126 game schedule. J. P. Friend news service of Blytheville, Arkansas, began what would become a continuing relationship with the league as the official statistician for the league. The salary limit was raised to $1075 per month and the team player limit raised to 15.

Although all of the 1938 league teams were present for the meeting, and all eight had posted the required guarantee money, Lexington was a question mark for the 1939 season. They had conducted talks with Paris, Tennessee, regarding the sale and transfer of their franchise. Bowling Green, Kentucky, attended the meeting and expressed interest in joining the group. Paris was ultimately unable to find a suitable playing facility, and the Lexington franchise was sold and transferred to Bowling Green. The team selected Rip Fanning to accompany the club along with several of the Lexington players. The team nickname was the Barons. For the first year Bowling Green would operate as an independent.

Meanwhile most of the other teams had lined up support from higher level teams. Fulton signed with the Detroit tigers via the Beaumont, Texas team. As a result, the Fulton team adopted the name Tigers for the 1939 season. Mayfield kept their arrangement with the St. Louis Browns, and Hopkinsville remained with Milwaukee. Owensboro was set with the Boston Bees (Braves), while Paducah was recently signed with the Brooklyn Dodgers. Union City returned to the folds of the St. Louis Cardinals. Early in 1939 it was announced the Cardinals would play the Greyhounds in an exhibition game in Union City on April 14.

This spring was unlike any past springs since the Greyhounds joined the league. Each year there had been professional baseball in Union City, and even before, there were teams involved in spring training at Turner Field. In 1939 the Greyhounds took spring training in Springfield, Missouri, with all the other St. Louis Cardinal farm teams. The number of agreements was substantially reduced that year, and Union City probably would not have been able to connect with them except for the success of the prior relationship, Branch Rickey's fondness for the town, and the hard work of Greyhound officers, Cecil Moss and Morgan Sedberry.

Since the Greyhounds were training in Springfield no one knew much about the 1939 team before they arrived in town on April 12. The Cardinals arrived on April 14, at 12:30 PM via the Nashville, Chattanooga, and St. Louis Rail Road. They were scheduled to depart after the game on a private train traveling on the Mobile & Ohio Railway. All seats were sold for the game and many requests by out-of-towners had to be turned down. The admission prices were posted as $.75 for general admission. A reserved grandstand seat went for $1. The grandstand box seats sold for $1.25, and children were admitted for $.40. The local club realized a bonus from the game in that all fans buying a season reserved seat in the grandstand had that seat for the Cardinal game.

Several thousand fans filled Turner Field to see the major leaguers put a 17-3 whipping on the local team. Among the players on the Cardinal team were Pepper Martin and Lon Warneke, who took over the public address system and gave a play by play to the crowd. Also on the team was the leagues leading hitter, Joe Medwick. He went three for four that day. Enos Slaughter, another future hall-of-famer, was a 22 year old second year player in the beginning of a great career. Paul Dean, brother to Dizzy, was also in Union City for the game as he attempted a comeback in 1939.

Union City's manager for the '39 season was Lee Johnson, a first baseman. Other managers in the league included Hugh Wise returning at Owensboro; Benny Tate again in Mayfield; Moon Mullins with Jackson; and Ben Tincup making a return to Paducah after a two year absence.

Wise was an individual worthy of special mention. He had been the owner, manager, and president of the Owensboro club when he moved the franchise from Portageville. Shortly after he sold the team, but managed to retain the manager position. He had great influence in the overall management of the organization. It was Wise, who convinced Bowling Green to come into the league. Owensboro was the largest town in the league and drew the largest crowds. One of the basic ideas in forming leagues was to have a number of towns that would be located close enough together that home fans would follow their team on the road. Until Bowling Green came into the league the closest town to Owensboro was Hopkinsville. With Lexington leaving the league the next closest team to Jackson was Union City, a town sixty miles away. Wise also served on the committee to set the season schedules. Initially this worked against him because the schedule had been approved with Lexington acting as the natural rival of Jackson. Natural rivals were scheduled to play each other on opening days and on all holidays. With the move of Lexington to Bowling Green, Wise wanted a change to allow Owensboro to be the natural rival of the Barons. The other league members voted to keep the schedule as it was. This required Jackson to play Bowling Green on opening days and holidays. This helped Jackson due to the large crowds attending the Bowling Green games.

Ben Howard did an excellent job as president of the league. One of the real problems always centered around the poor officiating. Since the umpires were often poorly trained, their performance matched this deficiency. Poor umpiring caused many "rhubarbs", resulting in loud, often profane arguments between the "men in blue" and players and managers. While some heated discussions was good for the gate, sometimes it got so bad it became offensive to the gentler folks in the stands. Union City's manager, Red Lutz, was suspended by Judge Bramham for 120 days in the 1938 season for pushing an umpire. Although this was later reduced to 90 days, Mr. Howard did not want a repeat and took action to avoid them. One of his first moves was to sign a large number of umpires on a tryout basis. Just as each team was allowed to carry players over the limit for the first 20 days of the season, Howard proposed to do the same with the umpires. He signed John Jurick, Chistropher, Illinois; Guy Hood, Oseceola, Indiana; Tim Floyd, Macon, Georgia; Loyd Rogers, Metropolis, Illinois; Pete DeLong, St. Louis; J. D. Godrey, Tupelo, Mississippi; D. W. Moore, Rock Island, Illinois; John Jolly, Murfreesboro, Tennessee; Randolph Settle, Washington, DC; James Clark, Rolla, Missouri; D. J. Harbin, Louisville; and A. J. Myer, San Antonio, Texas. He proposed to evaluate the umpires for the first month, then renew the contracts of only the best. He also set a standard for behavior in the league and let managers know that past performances would not be tolerated.

At least three of last year's umpires were moving up to higher classifications. Ranny Throgmorton, Mayfield, and C. C. Forrest, Fulton, were going to the Georgia-Florida League. Ellis Beggs was signed to officiate in the Cotton States League. In 1939, Joe Grace, a former slugger with Paducah, became the first Kitty leaguer to make it to the majors since the reorganization in 1935. After three years in Memphis, he was sold to the St. Louis Browns and became a starter. Union Citian, Walter Ward's contract was sold by the Cincinnati Reds to Columbia in the Sally League, but he spent most of the year in Bassett, Virginia, in the Bi-State League.

The opening day roster of the 1939 Greyhounds was filled once again with a group of names largely unknown to the Union City fans. Included were pitchers John Riley, Adrian Thebeau, Clalence Benac, Lloyd Fisher, and Joe O'brien; infielders, Dick Disney, Glenn Crawford, Billy "Pee Wee" Lowe, popular returnee Cy Redifer, and manager Lee Johnson; catchers, Tim Henville and Phil Cogswell; and outfielders, Les Findeiss, Oscar Riley, Lou Kotch, and Robert Scruggs. Union City won the first game against rival Fulton Tigers by a score of 8-6 with 900 fans in the seats. It was the first opening day game victory the Greyhounds had enjoyed since joining the league. It was not the omen fans hoped. The Hounds returned the favor to Fulton the next night in the Tiger park by losing 6-5. This was the last time in 1939 the team was at the .500 mark. They followed with eight more loses before gaining their second win, and held sole possession of the cellar spot.

By the end of May only four of the players who started the season were still on the roster. New names included John Flannery, Chancey "Lefty" Scott, John Ganczar, Harry Hildebrand, and Elbert Hodge. Hodge was a schoolteacher from Horn Lake, Mississippi, who had pitched great for the Greyhounds in previous seasons. He could join the team only after school dismissed for the summer months. Other players came and went, but the record at the end of May was 4-20. In mid-June the team came out of the cellar with a 10-28 record and was replaced by Fulton. Owensboro led the league with 24-13. Charlie Martin signed as a catcher, Louis Ariola came to play shortstop. Local furniture salesman, Harold Fuller, helped out first as a substitute umpire, then signed as a catcher for a few games. Malcolm and James Mathews, not related played the outfield, along with Jack Popenis. They could not stop the bleeding.

Owensboro continued to lead the league on July 4, and earned the right to host the all-star game which they won 8-2 before 3100 fans. The Greyhounds only representative was Elbert Hodge. Shortly after Hodge, sporting a 8-4 record, had to leave the team to attend a session at Peabody College in anticipation of becoming the principal and coach at Horn Lake, Mississippi.

Another all-star was pitcher Ellis Kinder of Jackson. A youngster from Arkansas, he was signed to a contract by Jackson, and since the Generals had no agreement with higher class teams, he was their sole property. Jackson sold the New York Yankees an option on Kinder for $1500 dollars. If they did not keep him, Jackson would keep the money, and Kinder would return to Jackson. Vernon Stephens played third base for Mayfield, and led the league in hitting. A few years later he would be playing for the Boston Red Sox.

The Greyhounds returned to last place in July and the local sports editor, Massey, was so disgusted with the clubs play and the fans attendance, he stopped publishing the standings or box scores in the paper. By July 29 the lead sports story was the appearance of female wrestler Mildred Burke. When the season ended he wrote that it was a good thing the Greyhounds were not in the playoffs, "it might interfere with the horse show, or something".

There was an appreciation night for Ben Howard on August 18 drawing 1300. The Greyhounds lost 4-1 to the Mayfield team. On the same night Owensboro drew 5,932 against Bowling Green to set the record for the largest crowd to ever see a Kitty League regular season game.

On September 2, 1939, Germany invaded Poland, and on September 4, England declared war on Germany. The curtain came down on the 1939 Kitty League season with the following standings: Mayfield 76-49, Owensboro 75-51, Bowling Green 75-51, Jackson, 67-59, Paducah 58-68, Hopkinsville 57-68, Fulton 52-74, and Union City a dismal 43-83 finishing 33 games out of first place. The Greyhounds lost 35 games by one run. In the playoffs Bowling Green defeated Owensboro in three straight, while Mayfield was handling Jackson 3-2. Bowling Green then won the 1939 championship by beating the Browns, four games to two.

For all the misfortune of the Greyhounds the season was successful from a league point of view. Much credit was given to president Ben Howard for having the league finish for the first time the entire season and playoffs according to schedule, and with the same eight teams starting the year. For the first time the league ended the season with all bills paid and a surplus of $1500 in the bank. Almost $12,000 passed through the league office in 1939. For his fine service Howard was given a $400 bonus and re-elected to another term. Popular Shelby Peace was again named vice president. Representatives present for the meeting held at Boyette's on Reelfoot Lake were Cecil Moss, Union City, K. P. Dalton, Fulton, J. C. Miller, Owensboro, B. B. Hook, Paducah, W. L. Harrington, Mayfield, Vick Smith, Bowling Green, and Harvey Gilland, Jackson.

The 1939 season saw total attendance figures of 260,540 pass through the Kitty League gates. The breakdown by team was Owensboro, 54,653 at Miller Field; Bowling Green, 45,145 at Fairground Park; Mayfield, 32,760; Paducah, 26,691 at Hooks Park; Hopkinsville, 23,287; Union City, 21,157 at Turner Field; Jackson 19,672 at Lakeview Park; and Fulton 17,945 at Fairfield Park.