In 1989, working with Eastman Kodak and R.R. Donnelley, McGraw-Hill introduced Primis Custom Publishing—the first customized publishing system to allow professors to design their own textbooks. In the 1990s, Primis' share of the market grew to 18.5% and it was acknowledged as the leading U.S. custom publisher. In 1995, McGraw-Hill unveiled a new corporate identity campaign and became The McGraw-Hill Companies. The corporation also reorganized its divisions to align its businesses behind three fast growing segments—education, financial services, and information and media. The corporate Internet site was also launched in 1995, and a corporate Intranet site was created in 1996, the same year revenues reached $3 billion.

Joe Dionne retired as CEO in 1998 and was succeeded by Harold W. (Terry) McGraw III, bringing the leadership of The McGraw-Hill Companies back to the McGraw family. The son of Chairman Emeritus Harold McGraw Jr., Terry has been with McGraw-Hill since 1980. Under Terry McGraw, the critical issues of copyright/database protection and e-commerce have taken center stage. Similarly, The McGraw-Hill Companies' groundbreaking privacy policy has become a model for other companies to follow. In 1999, on the strength of businesses like Standard & Poor's, BusinessWeek and McGraw-Hill Education, the corporation achieved its seventh consecutive year of record financial performance and reached an all-time high of $4 billion in revenue.

In 1999, the corporation celebrated the 125th anniversary of two of its longest running publications, Engineering News-Record and Electrical World. Started during the industrial revolution, those publications were leaders in reporting on new developments, while providing information in a variety of formats. Taking advantage of the Internet, BusinessWeek expanded its online presence with BusinessWeek Online. The corporation also leveraged the content of Standard & Poor's and BusinessWeek with the issuance of S&P Personal Wealth, and strengthened its medical publishing unit by purchasing Appleton and Lange. In addition, the corporation streamlined its operation by selling four chemical magazines and two Italian publishing companies.

During 2000, The McGraw-Hill Companies' three segments witnessed global growth in a variety of areas. The Financial Information Services segment expanded in non-traditional ratings services, corporate governance in emerging markets, and added new products to the S&P Indexes. The K-12 education business increased its market share and developed new products for higher education and testing. The Information & Media segment continued growth internationally and achieved record advertising sales. For example, new online portals were created to serve the aviation, energy and construction markets. Streamlining of the corporation's business continued with the sale of Tower Group. Acquisitions of the Mayfield Publishing Company and Tribune Education contributed to further development of size and scale in the Education business.

In spite of the challenging economic conditions in 2001, the corporation achieved success in its Financial Information Services and Education business units, but not in the Information & Media area. McGraw-Hill Education continued its push for innovative learning materials with the McGraw-Hill Learning Network's new digital products. The acquisition of Frank Schaffer Publishing and the integration of Tribune Education products strengthened the children’s publishing arena. Standard & Poor's acquired Corporate Value Consulting from PricewaterhouseCoopers, adding significant new capabilities. The acquisition of FT Energy strengthened Platts' present offering of products.

Solid performances in Financial Services and by the McGraw-Hill Higher Education, Professional and International Group, improvement in the advertising market and prudent cost controls helped the Corporation achieve double-digit growth in a challenging year. In addition to its continuing emphasis on global growth and product diversification, Standard & Poor's continued to provide leadership to its markets. It introduced a new methodology for evaluating companies' "core earnings" and published a study and rankings on corporate transparency, governance and disclosure practices. McGraw-Hill Higher Education grew at double-digit rates and its products sold well worldwide. In the U.S. McGraw-Hill School Education Group captured 32% of the K–12 (students ages 4-17) adoption market versus 29% in 2001. Although it was a challenging environment, Information & Media continued to serve new markets with partnerships and offerings such as BusinessWeek TV, which is now broadcast in 188 U.S. markets, and the Homeland Security Conference and Exposition. Platts' successful integration of FT Energy enabled it to provide new capabilities in the areas of database, research and consulting services, while McGraw-Hill Construction rebranded itself and delivered a strong bottom line performance. Finally, BtoB magazine recognized the strength of the Corporation and the success of its strategy by naming The McGraw-Hill Companies No. 1 on its "Top 10 Business Media Powerhouses" list.