The history of Le Moyne Dolphins men's basketball from 1958 to 1960 includes the Dolphins' first two appearances in the NCCA tournament. Led by Dick Lynch, Bob Hollembaek and Chuck Sammons, Le Moyne won a share of the 1959 Middle Eastern College Athletic Association (MECAA) championship, the first conference title in program history and earned the first of what would be seven NCAA tournament bids over a span of 11 seasons. Lynch, John Caveny and Bill Stanley led the Dolphins to the outright MECAA championship in 1960, and a second consecutive tournament berth. Head coach Tommy Niland was named MECAA coach of the year for both 1959 and 1960. The Dolphins were 18–6 in 1958–59, reaching the Sweet 16 of the 1959 tournament, and 13–5 in 1959–60, finishing fourth in their region in the 1960 tournament. Lynch was named first-team all-MECAA in both seasons.

First NCAA tournament bid (1958–1959) The 1958–59 season marked the start of a golden era for Le Moyne Dolphins basketball. They appeared in seven of the 11 NCAA College Division tournaments between 1959 and 1969, reaching the Sweet 16 in 1959 and 1964.

During the preseason in the fall of 1958, the outlook was less than rosy. Although Le Moyne's leading scorer, Dick Lynch, was returning for his junior season, the team was thought to be undersized and lacking enough rebounding and depth to be competitive. Captain Frank Bergen, top rebounder John Young and Ed Czajka all graduated. John Dobbertin, Dick Nendza and Dennis Morrissey returned for their senior seasons, and Bob Scarborough, who missed a season due to academic ineligibility, returned as a redshirt senior. In addition to Lynch, other returning juniors were George Woyciesjes, Bill Young and John Finnegan. Bob Hollembaek, who withdrew from Le Moyne in January 1957, because of academic difficulties, re-enrolled and returned for his senior season. Chuck Sammons and Bob Bostick, who would become Le Moyne's first black varsity player, competed for a starting role during the preseason, but Bostick was hampered by injuries. Practices started at Grant Junior High School in October and moved to the armory in November. The team scrimmaged against Albany State (NY), Cornell and Ithaca. Morrissey was named captain. Tommy Burns, a sophomore transfer from Georgetown, was not eligible to play until the January 24 game at Saint Michael's because of NCAA transfer rules.

Turnovers and rebounding doomed the Dolphins in their December 1 season opener against Villanova at the Palestra, an 83–67 loss. After trailing by seven points at halftime, the Dolphins got within six points at 39–33 with a minute and a half gone by in the second half. The Wildcats extended the lead to 11 points, but two straight baskets by Dick Nendza, who finished with 12 points off the bench, brought Le Moyne back within seven points at 49–42 with 13:42 to play. Led by their captain, Joe Ryan, who scored four baskets in a 68-second stretch at one point, Villanova cashed in their fast-break opportunities created by a string of errant Le Moyne passes and had a 20-point bulge five minutes later, putting the game out of reach. The size-challenged Dolphins were outrebounded, 67–28. Dick Lynch scored 20 points and grabbed 12 rebounds to lead Le Moyne, but he shot only 8 for 21 from the floor. Sophomore Bob Bostick made his varsity debut, becoming the program's first black player; he scored one point in limited action.

Sophomores Dave Rose, Frank Graziadei and Ron Januszka were added to Le Moyne's list of available players following the Villanova game.

After watching his team fall behind Oswego State, 44–34, in the Dolphins' home opener on December 6, coach Tommy Niland sent 5'11" sophomore Bob Bostick into the game at center to substitute for fellow sophomore Chuck Sammons. Bostick, who finished with six points, provided the spark Le Moyne needed, inspiring the Dolphins with his rebounding and defense. A spectacular out-of-bounds save and pass by Bostick to Dennis Morrissey led to a layup that brought Le Moyne within a point at 54–53. After the Lakers turned the ball over on the ensuing possession, Bostick's jump shot gave the Dolphins their first lead of the second half with 2:55 to play. John Dobbertin's free throw made it a 22–10 run. After Oswego State tied the game at 56, Dick Lynch's free throws gave Le Moyne the lead with 45 seconds left. Ron Davis, who had a game-high 18 points, missed a jump shot on the Lakers' next possession, and Dobbertin hit another pair of free throws to put the game out of reach, as the Dolphins held on for a 62–57 victory. Dick Lynch scored 15 points to lead Le Moyne. The game was interrupted by a brief scrap between Davis and Bob Hollembaek that led to both benches clearing and fans spilling onto the floor, before order was restored by the officials. No one was ejected. In a separate incident at halftime, groups of Le Moyne and Oswego State fans got involved in a scuffle on the court, which was broken up by armory staff.

Just two games into the season, Le Moyne lost starting senior playmaker John Dobbertin, who suffered torn knee ligaments in a tobogganing accident. He was expected to miss at least a month.

Hours before the Dolphins' December 13 home game against Saint Peter's, Bob Bostick left the team, citing financial reasons. Left without a backup at center, Chuck Sammons responded with a double-double, playing all 40 minutes while scoring a team-high 17 points, grabbing 10 rebounds and hitting the deciding jump shot with two seconds to play in a 70–68 Le Moyne victory over the Peacocks, a team that had played in the NIT each of the previous two seasons. Sammons scored nine of Le Moyne's final 11 points of the game. Saint Peter's built an eight-point lead in the first half, but the Dolphins, fueled by the aggressive defense of Dennis Morrissey and the strong rebounding of Dick Lynch, went on an 18–9 run over the final seven minutes to claim a one-point lead at the break. Dick Nendza had six points during the run, and Morrisey and Lynch each added four. After the Peacocks switched to a frustrating zone defense and took a five-point lead early in the second half, Le Moyne regained their composure. The game was tied five times over the final six minutes, but the Dolphins appeared to have the edge when they took a 67–63 lead with 2:10 remaining. However, Saint Peter's tied the game with 1:17 to play. Le Moyne froze the ball for 1:15 and began looking for Lynch for the final shot in the closing seconds. However, Lynch was well covered, and he passed the ball to Bob Hollembaek, who found Sammons open on the left side for the game winner. The Dolphins improved to 2–1 on the season and 1–0 in MECAA play.

The Dolphins traveled to Burlington, Vermont for the Saint Michael's Invitational Tournament on December 18, and drew the host in the opening round. Saint Michael's had been the runner-up in the 1958 College Division tournament and was ranked no. 9 in the small college poll. Four of the six players in their rotation from the previous season were still with the team. Dick Lynch scored 18 first-half points to power Le Moyne to a 37–35 lead at the break. Hank Gretkowski, who was the Knights' top rebounder and led them with 24 points, was charged with the task of guarding Lynch in the second half and slowed him down a bit. With the Dolphins leading, 41–39, early in the second half, Saint Michael's embarked on a 9–0 run and seized control of the game. Le Moyne made a run and got within two points at 59–57 with five minutes to play, but the Knights scored the next four points, and the Dolphins succumbed, 71–63. Lynch scored 12 points in the second half to finish with a game-high 30. Lynch had 14 field goals in the game, all coming on jump shots.

The following night, the Dolphins took control of the consolation game against Assumption early and romped to a 75–61 victory. The easy win took Dick Lynch out of consideration for the tournament's most valuable player award, as he played just over half the game and finished with 14 points, doing more passing than shooting. Dick Nendza scored a game-high 22 points for Le Moyne, who led by 21 points at halftime and by as many as 25 points in the second half. Bill Young started at center in place of Chuck Sammons, who missed the game with a cold, and scored 21 points.

Playing on the third straight night and in their fifth game in eight days, the Dolphins came out strong, sparked by Dick Lynch's 15 first-half points, in their December 20 game at Siena, building a 15-point lead and holding a nine-point edge at intermission. The Indians used a full-court press in the second half to get back into the game and sent it to overtime with the score tied at 53. The tired Dolphins appeared to be on the verge of a loss, playing without Chuck Sammons, who missed his second straight game with a cold, and losing the services of Bob Hollembaek, Dennis Morrissey and Dick Nendza, all of whom fouled out during the overtime period. With Le Moyne trailing, 65–62, in the final minute, sophomore Dave Rose, finding himself in a crucial spot with the Dolphins short on manpower, hit a jump shot, his first basket of the season, to cut the deficit to one point. On Siena's next possession, the Dolphins forced a turnover, and Lynch grabbed the loose ball and was fouled with three seconds on the clock. Lynch, who finished with a game-high 25 points, hit both ends of the one-and-one to give Le Moyne a 66–65 victory, improving their record to 5–2 overall and 2–0 in MECAA play. This was Le Moyne's 26th all-time win over a University Division/major program.

John Dobbertin had the cast removed from his injured knee in late December, but he was not expected to be available to play until early February. John Finnegan suffered a knee injury in practice in early January and was expected to miss two weeks.

John Dobbertin returned to action with his right knee heavily bandaged on January 31, and sparked a rally that pushed the Dolphins to a 74–61 home victory over St. Francis (NY). Dobbertin, usually a playmaking point guard, entered the game with 11 minutes to play and Le Moyne leading, 50–48. He exploded for 13 points during an 18–7 run over seven minutes that gave the Dolphins a 13-point bulge. Dick Nendza and Chuck Sammons joined Dobbertin with a team-high 13 points for Le Moyne. The Terriers played a box-and-one defense with Fred Schneider closely guarding Dick Lynch and holding him to just seven points on 3-for-6 shooting. Two of Lynch's baskets were on tip-ins following offensive rebounds. Senior Bob Scarborough made his season debut but played only briefly; it was his only appearance of the season and the final game of his collegiate career. Sophomore transfer Tommy Burns, who had played the previous two games after satisfying the NCAA waiting period, missed the game with the flu. The Dolphins improved to 9–3 overall and 3–0 in MECAA play. This was Le Moyne's 27th all-time victory over a University Division/major program.

The flu bug swept through the Dolphins following the St. Francis game. In addition to Tommy Burns, Dick Nendza, Chuck Sammons and Ron Januszka were unable to attend classes or practice. A doctor advised John Dobbertin to rest his right knee three days after his seven-minute appearance. Bob Hollembaek jammed his finger in the St. Francis game. The day before the team's next game, a February 7 home tilt against Gannon, only the status of Sammons remained doubtful, but coach Tommy Niland was hopeful he would be able to play. Sammons, Burns, Nendza and Dobbertin all played in the Gannon game with Sammons topping the wounded warriors, scoring 12 points. Dick Lynch had a team-high 16 points, leading the Dolphins to a 58–52 win. Lynch was also Le Moyne's top rebounder with 11 boards and the primary defender on Gannon's top scorer, Pete Russo, holding him to eight points on 4-for-24 shooting.