The 2nd tournament, official name: SASUKE1998秋 (literally Sasuke 1998 Fall) was the first tournament held outdoors, at TBS Midoriyama Studios. While there were no new obstacles added to the First Stage, the time limit was reduced by 10 seconds. While there were almost no changes in the Second Stage, the Pipe Slider made its debut here and remained a Third Stage staple until SASUKE 17.

SASUKE 3, official name: SASUKE1999春 (literally: SASUKE 1999 Spring), was the third SASUKE tournament, airing in Spring 1999. Three new obstacles were added to the First Stage: The Rolling Log, Tarzan Jump and Rope Climb.

The fourth tournament, official name: SASUKE1999秋 (literally SASUKE 1999 Autumn), is statistically the most successful tournament in SASUKE history, in which many records were set. In Third Stage, two new obstacles were introduced: Arm Bike and Cliffhanger.

The 5th Competition, official name: SASUKE2000春 (literally SASUKE 2000 Spring). The course underwent a modest renovation. In the First Stage, the Jump Hang and Soritatsu Kabe were added, quickly earning reputations as feared obstacles. The Soritatsu Kabe has been used in every tournament since then with the exception of some tournaments later. In the Second Stage, a new first obstacle, the Tackle Machine pushed the previous first obstacle, the Spider Walk (which received a modification), to the second position. The Body Prop was the only new obstacle added in the Third Stage, but unlike the Tackle Machine of the previous stage, the Body Prop became a threat to many competitors and was not removed until SASUKE 18.

The 6th Competition, official name: SASUKE2000秋 (literally SASUKE 2000 Fall). In the First Stage, the Jump Hang was particularly deadly. The First and Third Stages remained unchanged, but the Second Stage added the Narrow, which replaced the Tackle Machine.

The 7th Competition, official name: SASUKE2001春 (literally SASUKE 2001 Spring). For the second straight tournament, the First and Third Stages were unchanged. However, due to the 100% completion rate of the Second Stage in the previous tournament, the stage underwent a large redesign. The first two obstacles were replaced with the Chain Reaction and Brick Climb (not an official obstacle), and a revamped Spider Walk, as well as the conveyor belt being modified. The time limit was raised to 90 seconds.

The 8th Competition, official name: SASUKE2001秋 (literally SASUKE 2001 Fall) was arguably one of the best and emotional tournaments. For the whole tournament, Typhoon Nari showered Midoriyama in rains, causing several long rain delays. The rains also caused the course to be very slick, affecting the performance of competitors. This tournament introduced a new first obstacle, the Godantobi (which would later become the basis for many other obstacles throughout SASUKE).In the Second Stage, the time limit was raised to 100 seconds, the highest Second Stage time limit in history at the time. Due to the rains, the electric Gyakusō Conveyor had to be halted to prevent shocking the competitors who crossed it, making the obstacle far easier. Starting in this tournament, a button was added at the finish line, and competitors were required to press it in time in order to stop the clock, open the gate, and advance to the Third Stage.

The 9th competition, official name: SASUKE2002春 (literally Sasuke 2002 Spring). It was remembered most for its redesigned Third Stage, featuring perhaps the most iconic incarnation of the Cliffhanger (the Cliffhanger Kai), the introduction of the new Rumbling Dice and Lamp Grasper. The First Stage remained unchanged since SASUKE 8. The Second Stage's time limit received a cut of 20 seconds.