Osiander was an assistant coach with the California Surf of the North American Soccer League (NASL).

Osiander eventually returned to San Francisco, becoming a waiter at Graziano's, a local restaurant, while playing and coaching in the city's highly competitive soccer leagues.

In 1985, he coached a semi-pro club, the San Francisco Greek-Americans, to the National Challenge Cup title.

Back in 1974, the United States Soccer Federation (USSF) had hired Osiander as part of its coaching staff.

In 1978, the U.S. Olympic committee inaugurated a National Sports Festival, hiring Osiander as the West team soccer coach.

The U.S. went on a tear in the second round, going undefeated against Trinidad and El Salvador, outscoring its opponents 13 to 4, and winning a spot in Seoul.

On January 16, 1989, USSF released Osiander when it announced the hiring of Bob Gansler as the full-time national team coach.

In 1991, Osiander coached the U.S. U-23 team to a gold medal at that year's Pan American Games, held in Cuba.

In one of the many inexplicable moments in U.S. soccer history, Osiander benched his leading scorer, Steve Snow, for the team's first Olympic match.

While working at Graziano's, he had spent time as an assistant coach with the San Francisco Bay Blackhawks of the American Professional Soccer League (APSL) before it folded in 1992.

Despite finishing the regular season fourth out of six, the Ruckus made it to the A-League championship series, only to fall to the Seattle Sounders.

Osiander's success with the Greek-Americans and Ruckus brought him to the attention of the newly created Major League Soccer club Los Angeles Galaxy which hired him as its first coach.

In September 1999, the San Jose Clash hired Osiander to replace Brian Quinn near the end of the 1999 season.

At the time, Osiander was leading the Project 40 team into the United Soccer League playoffs where it lost in the semifinals to the Minnesota Thunder.

[citation needed] He also temporarily took over for the U-19 Tri-Valley Arsenal, due to the absence of former coach Terry Weekes.