Pioneer High School has a proud men's tennis history, reaching back into the era when Ann Arbor High School occupied the current Pioneer buildings in the 1960s and beyond.

Under Coach Donald Drake, Ann Arbor High took the Class A Men's Tennis Singles Championship in 1940 and the Men's Tennis Doubles Championship in 1941. During the 1950s and 1960s, when Jean Hoxie's famous Hamtramck teams were utterly dominant, winning 17 out of 20 (if you don't know about the Hamtramck teams and the "Robin Hood of Tennis" who established what may have been the world's first tennis academy in working class Detroit, check it out), Ann Arbor University High was runner-up in 1962 and Ann Arbor High was runner-up in 1967. With the creation of Huron High, Ann Arbor High became Pioneer and was runner-up to Hamtramck again in 1969.

It wasn't until 1989 that Pioneer achieved runner-up status again, this time to Okemos.

With the 1990s began a period during which Pioneer has been a perennial men's tennis power. The first Class A Men's Tennis Championship came in 1990 under Coach Tony Verbanac in his last year. 1991 saw the beginning of the Pullen era in Pioneer tennis, as Tom "Brick" Pullen coached the first of his many state championship teams. Pioneer was runner-up to Okemos in 1992, champion again (shared with Bloomfield Hills Lahser) in 1993, and then runner-up to Ann Arbor Huron in 1996.

Michigan High School Tennis was restructured in 1997, with Pioneer going into Division I. In the seven years of the new divisional play, there have been only two champions of Division I: Brother Rice and Pioneer. Brother Rice were champions in 1998-2000, Pioneer and Brother Rice shared the 2001 championship, and Pioneer was champion in 2002-2006.

The 2002, 2005, and 2006 State Championships were especially notable. In 2002 Pioneer won seven out of eight flights and thirty-nine out of a possible forty matches and Pioneer's number one singles player, Adam Monich, held a 4-0 lead on Brother Rice's Matt Christian in the third set tiebreak before cramps set in and he was unable to win another point. (Ed.: Two years ago, I wrote, "It seems almost unimaginable that this record will ever be equaled.)  However, that very year, in 2005, Pioneer won 39 out of 40 matches again, and in 2006, Pionner racked up 37 out of 40.

Coach Pullen was named Women's Coach of the Year in 2003 and Men's Coach of the Year in 1999 and in 2006.