| SERENAWILLIAMS | 27-/37-Across won her first Grand Slam title (the 2018 US Open) by defeating this tennis legend: 2 wds. |
| MADISONKEYS | This American won her first Grand Slam title in Melbourne at last month's Australian Open |
| AUSTRALIANOPEN | In 2019 27-/37-Across won her second Grand Slam title at this Melbourne tournament: 2 wds. |
| ROGERFEDERER | Swiss tennis legend: 2 wds. |
| CHRISBOHJALIAN | Midwives novelist who wrote 16-Across and 27-/37-Across: 2 wds. |
| MORITZ | Where #37-Across won Olympic gold in Switzerland in 1948, St. ___ |
| GAUFF | Coco, tennis player who won her first Grand Slam singles title at the 2023 U.S. Open (5) |
| NAOMIOSAKA | The first Japanese tennis player to win a Grand Slam singles tournament, defeating Serena Williams in the 2018 US Open final (5,5) |
| STEFFIGRAF | Which tennis player won her first Grand Slam singles in 1988 and last in 1999? (6,4) |
| TEEN | Serena Williams, agewise, when she won her first Grand Slam |
| STANISLASWAWRINKA | Tennis player who won his first Grand Slam singles title at the 2014 Australian Open (9,8) |
| SAMPRAS | Tennis player Pete ___ won his first Grand Slam when he won the U.S. Open in 1990. |
| SINNER | Jannik, tennis player who won his first Grand Slam singles title at the 2024 Australian Open (6) |
| PATRAFTER | 2002's award was won by this tennis star; he won the US Open in 1997 and 1998 |
| SERENA | She defeated Martina in 1999 for her first Grand Slam singles title |
| STAN | Identify the first name of this tennis player who became the oldest male to be given a wildcard at the Australian Open. (4) |
| RADUCANU | Who was the last British tennis player to win a Grand Slam title (US Open women's singles 2021)? (8) |
| OSAKA | WTA World No. 1 who defeated Serena Williams at the 2018 US Open (5) |
| EDBERG | Stefan, whose first Grand Slam tennis title was the Australian Open in 1985 (6) |
| DOUBLEBAGEL | Iga Swiatek won the Wimbledon ladies' singles title on July 12 by defeating Amanda Anisimova, 6-0, 6-0, a lopsided tennis score nicknamed this |
