He lost in the second round of the Australian Open to Ramesh Krishnan, the quarterfinals of the French Open to Andrei Chesnokov, the quarterfinals of Wimbledon to John McEnroe (7–6, 3–6, 6–3, 6–4), and the second round of the US Open to Pete Sampras (5–7, 6–3, 1–6, 6–1, 6–4). He did not win a tournament during 1989 and he finished the year ranked World No. 12. Wilander briefly moved back into the top 10 rankings on 12 February 1990, but by the end of the year, his ranking had slumped to World No. 41. He defeated Boris Becker in the quarterfinals of the Australian Open, only to lose to Stefan Edberg in straight sets in the semifinals. He skipped the French Open and Wimbledon and lost in the first round of the US Open to Brad Gilbert. Wilander played only the first half of 1991. He lost in the fourth round of the Australian Open and the second round of the French Open. He finished the year ranked World No. 159. Wilander was absent from the tour in 1992. He played seven tournaments in 1993, losing in the first round of five of them. At the US Open, he lost in the third round to Cédric Pioline. He finished the year ranked World No. 330. Except for Wimbledon, Wilander played a full schedule in 1994. He lost in the fourth round of the Australian Open to MaliVai Washington, the first round of the French Open to Andre Agassi (6–2, 7–5, 6–1), and the first round of the US Open to Guy Forget. His only victory over a top ten player was in the second round of the tournament in Indianapolis against Todd Martin. He finished the year ranked World No. 129. Wilander's results improved slightly in 1995 as he finished the year ranked World No. 46. After losing in the first round of the Australian Open to Jacco Eltingh, he lost in the second round of the French Open to eighth ranked Wayne Ferreira 6–7, 7–6, 6–3, 6–7, 8–6. He then lost in the third round of Wimbledon to Eltingh and the second round of the US Open to Martin. In other tournaments, he had wins against tenth ranked Marc Rosset, eighth ranked Ferreira, and sixth ranked Yevgeny Kafelnikov.