Chess Club was established in 1960-1961, the same year the school opened. According to the February, 1961 issue No. 3 of the Deerprints, Chess Club was created by a group of fourteen enthusiastic members. Chess club is made up of both the competitive and the pleasure-seeking, and higher-level players teach the lower-level ones. Although small, the group was growing rapidly and had high hopes of participating in district, state and national tournaments.

After suffering humiliating 6-2 and 5-1 defeats against Lake Forest Highschool in 1961, and then tying Evanston in 1962, the Chess Club began to pick up the pace in their 1963 school year. DHS Chess Club which had been growing in both members and skill, began winning against many schools in the area in 1963, starting with a historic tie against Lake Forest, due to a hard-fought win by club president George Pearson. Chess Club continued this hot streak and defeated HPHS in a 7 to 3 victory on February 8th, 1963. 

After losing a lot of their talent as a result of graduating seniors, the Chess Club had to sharpen their skills even more; newly elected president Bill Zimmer (Junior) helped create this new generation of chess players for DHS in 1964.