The first bowl game the Midshipmen participated in came at the conclusion of the 1923 college football season, when they were given a bid to play in the tenth edition of the Rose Bowl game. The Midshipmen, led by coach Bob Folwell, finished the regular season with five wins, one loss, and two ties (5-1-2). Their lone loss came at the hands of the Penn State Nittany Lions, falling 21-3. One of the Midshipmen's two ties came in the Army–Navy Game. Navy's opponents in the Rose Bowl were the Washington Huskies, who came in with a record of ten wins and one loss (10-1).
The game kicked off on January 1, 1924 in the Rose Bowl amidst the Tournament of Roses Parade. The first quarter went scoreless, but the Midshipmen scored twice during the second quarter: on a pass from quarterback Ira McKee and from a short run by McKee. The Huskies scored once on a long run from running back George "Wildcat" Wilson. The Midshipmen relied heavily on passing plays, while the Huskies relied on their running game the first half.
The third quarter also went scoreless. The Midshipmen effectively controlled the Huskies during most of the fourth quarter, until they fumbled the ball on their own 10-yard line. Washington scored on a trick play from the Midshipmen 12-yard line, tying the game. The Midshipmen tried to score, but turned the ball over at midfield. Washington took the ball down to the Navy 20-yard line, but were unable to score again. The Huskies missed a last-second field goal, and the game ended 14-14 tie.
The Midshipmen scored on the game's opening drive, off a three-yard run by running back Joe Gattuso. The Navy defense shut down the Ole Miss offense the first half, holding them to three first downs. The Rebels' longest drive during the first half went for a total of 16 yards. Neither team scored during the second quarter, although the Midshipmen managed to get within one yard of the Ole Miss goal line. Navy led at the half with a 7-0 lead.
Navy controlled the third quarter by running the ball repeatedly. On a fourth down conversion attempt from the Ole Miss 16-yard line, Midshipmen kicker John Weaver caught a pass from quarterback George Welsh in the back of the end zone, giving Navy a 14-point lead. The Midshipmen stopped the Rebels on their next drive, but Rebels quarterback Eagle Day punted the ball 72 yards to the Midshipmen 7-yard line. The Midshipmen drove down the field in three plays, and Gattuso ran the ball in for another touchdown from two yards out. The Midshipmen defense shut out the Rebels' offense during the fourth quarter. By the end of the game, the Rebels had gained 121 yards of total offense, compared to the Midshipmen's 442.
The 1958 Cotton Bowl Classic was played between the Navy Midshipmen and the Rice Owls on January 1, 1958. Coming into the game, Navy's record was 8-1-1 under head coach Eddie Erdelatz; Rice's was 7-3 under coach Jess Neely. The game was the only bowl that year to feature two of the nation's top ten teams: Navy was ranked fifth in the nation, while Rice was eighth. Approximately 75,500 spectators attended the game.
The game was expected to be a contest between quarterbacks Tom Forrestal (Navy) and King Hill (Rice), both of whom had been named to the 1957 College Football All-America Team. After Hill struggled early, however, he was replaced by Frank Ryan on the team's third possession. By the end of the first half, the Owls had managed only one first down, and the Midshipmen led 13-0. The Midshipmen extended that lead to 20-0 in the third quarter before Rice scored its only touchdown following an interception. The game ended in a 20-7 Navy victory; it was the Owls' first ever postseason loss. Navy's Tom Forrestal and Tony Stremic were named the game's MVPs. Both Forrestal and Ryan broke the previous bowl record for completions, set the previous year by Chuck Curtis, with 13 each.
Among the 71,218 attendees for the 1961 Orange Bowl was newly elected President John F. Kennedy. The game featured the fifth-ranked Missouri Tigers, who were the champions of the Big Eight Conference, and the fourth-ranked Navy Midshipmen. The contest quickly became a defensive battle early in the first quarter: Navy defensive back Greg Mather scored first for the Midshipmen after intercepting a lateral pass and running it 98 yards for a touchdown. Two drives later, Missouri's Norm Beal intercepted a pass and ran it 90 yards for another touchdown, making the score 7–6 at the end of the first quarter. The first offensive points of the game came when Missouri quarterback Ron Taylor ran in for a touchdown in the second quarter. halfbackJoe Bellino, who had won the Heisman Trophy earlier that year, was held to four yards of rushing for the game, although he did score a touchdown on a pass intended for another receiver late in the game. Navy finished the game with four interceptions, while Missouri fumbled the ball five times, losing possession three times.
The 1964 Cotton Bowl was played between the second-ranked Navy Midshipmen and the first-ranked Texas Longhorns. Navy was 9-1-0 and led by Heisman Trophy winner Roger Staubach. Texas was 10-0-0 and the AP national champion (the AP poll did not publish polls after the bowls at the time, so Texas was the season-ending AP #1 regardless of the outcome of the game). The game took place on January 1, 1964. Texas defeated Navy with a score of 28-6. The attendance was approximately 75,300. The game's MVP's were Texas' Scott Appleton and Duke Carlisle. Navy was coached by Wayne Hardin and Texas by Darrell Royal This was the first time the Cotton Bowl hosted both the #1 and #2 teams in the nation. It is just the second #1 vs #2 bowl game in college football history, the first being the 1963 Rose Bowl.
After playing a first half that saw both teams combine for a NCAA bowl game record 68 points, Navy defeated the California Bears by keeping them to a field goal in the second half. Midshipmen quarterback Chris McCoy completed 9 of 13 passes for 277 yards, setting NCAA bowl game records for most yards per pass attempt (21.3) and most yards per completion (30.8).
The Midshipmen entered the Emerald Bowl with a 9-2 record, its best win-loss record since the 1963 season. Against the New Mexico Lobos, the team jumped to an early 21-7 lead. In the third quarter, the Midshipmen began a drive that would eventually comprise 26 plays and use almost 15 minutes of game time, setting a new NCAA record for the longest drive in a college football game. The Midshipmen won the game with a score of 34-19, giving the team 10 wins for the season for the first time since the 1905 season. As a result of the win, the Midshipmen finished the season ranked 24th in both the Associated Press and the USA TodayCoaches' Poll. The game's attendance of 28,856, an increase of 28 percent over the previous year, also set an Emerald Bowl record.
The inaugural edition of the Poinsettia Bowl was played between the Navy Midshipmen and the Colorado State Rams. Navy's record was 8-3, while Colorado State's was 6-5. The game took place on December 22, 2005, and the Midshipmen defeated the Rams 51-30. The attendance was 36,842. Midshipmen Reggie Campbell, who tied the NCAA record for most points scored in a bowl game with 30, received the game's offensive MVP award. Navy's Tyler Tidwell won the Defensive MVP award. Navy was coached by Paul Johnson and Sonny Lubick led Colorado State.
The 2007 Poinsettia Bowl was played between the Navy Midshipmen and the Utah Utes. Navy had a record of 8-4. Utah also had a record of 8-4. The game took place on December 20, 2007. Utah defeated Navy 35-32. The attendance was 39, 129. The game's MVP was Utah's Brian Johnson. Navy was coached by Ken Niumatalolo. Utah by Kyle Whittingham.
^This was the inaugural Poinsettia Bowl, therefore giving it the highest recorded attendance at the time.
^Paul Johnson held the position of head coach at Navy until he was hired as the new head coach of the Georgia Tech Yellow Jackets prior to the 2007 Poinsettia Bowl. The school promoted Ken Niumatalolo to interim head coach and then made the position permanent prior to the bowl game.
^This was the inaugural EagleBank Bowl, therefore giving it the highest recorded attendance at the time.