High school males from fatherless households are less likely to receive the needed support to succeed in school than their peers from two parent households (Astone and McLanahan, 1991). Research indicated that the biological father's influence will sway the male child's overall development (Jones, 2004). This qualitative study explores the connections between fatherless households and school achievement among high school males. Its purpose is to enlighten school leadership about strategies for assisting high school males from fatherless households with obstacles that may affect their school performance. The grounded theory study includes findings from one-on-one interviews of seven adult males from fatherless households, ages 28 and older, with varying careers, education, and marital status backgrounds who currently work or previously worked in some capacity with high school males from fatherless households. During the interview, common words, responses, shared experiences, and patterns emerged that identified factors that contribute to the academic outcomes of high school male students. Findings include the following: 1) Relationships with the biological father, biological mother, as well as the relationship between the father and mother, have a positive or negative emotional effect on high school males; 2) High school experiences and factors, such as academics, attendance, discipline, and various obstacles were impacted by fatherless households; 3) The influences of biological and other adult males are critical to the academic success of high school males from fatherless households; 4) There are positive and negative factors that affect high school males from fatherless households; and 5) Various roles, strategies, and programs contribute to the academic success of high school males from fatherless households. In addition to these findings, this study identifies further research needed for educators to explore other facets of high school males from fatherless households and school performance. / Ed. D. / This research study explores the connections between fatherless households and school achievement among high school males. Its purpose is to enlighten school leadership, parents, and community about strategies for assisting high school males from fatherless households with obstacles that may affect their school performance. The study includes findings from one-on-one interviews of seven adult males from fatherless households, ages 28 and older, with varying careers, education, and marital status backgrounds who currently work or previously worked in some capacity with high school males from fatherless households. During the interview, common words, responses, shared experiences, and patterns emerged that identified factors that contribute to the academic outcomes of high school male students. Findings include the following: 1) Relationships with the biological father, biological mother, as well as the relationship between the father and mother, have a positive or negative emotional effect on high school males; 2) High school experiences and factors, such as academics, attendance, discipline, and various obstacles were impacted by fatherless households; 3) The influences of biological and other adult males are critical to the academic success of high school males from fatherless households; 4) There are positive and negative factors that affect the high school males from fatherless households; and 5) Various roles, strategies, and programs will contribute to the academic success of high school males from fatherless households. In addition to the findings, this study identifies further research needed to explore other facets of high school males from fatherless households and school performance.