While the history books may show that the era carried a bleak 126-162-1 record in its entirety, many positives occurred for the Middlebury Baseball program at this time. For example, an era of stability for head coaching in the program was emerging at the conclusion of the war, and this era saw fewer coaching turnovers than eras in the past. John Kelly began the era at the helm, first coaching three years (1941-43, 3 yrs, 9-25) before a year break at the beginning of the war in which his duties were relinquished to Arthur Brown (1944, 1 yr, 5-4), then returning to coach two more years in the mid-40s (1945-46, 2 yrs, 8-14) before leaving the school (5 yrs total, 17-39). Coach Richard Ciccolella, owner of the second best winning percentage in the programs history (.629), then adopted the program in 1947, starting a string of five straights state series championships. In total, Ciccolella concluded his stent as head coach after five years between 1947-1951 with a 44-26 record. Rounding out the era was coach Robert Sheehan. Sheehan, while lacking a winning record (1952-1962, 11 yrs, 60-93-1), gave the program the stability they needed by providing 11 years of service, exceeding any of his predecessors.

John Kelly (1941-43, 1945-46)Record: 17-39	Arthur Brown (1944)Record: 5-4 No Picture on Record
Richard Ciccolella (1947-51)Record:44-26	Robert Sheehan (1952-62)Record: 60-93