| 100% | SOLSTICE | 8 | June 21 in summer, December 21 in winter, usually |
| 39% | ATREE | 5 | What's clothed in summer and naked in winter, per an old riddle |
| 39% | SOLSTICE | 8 | Summer __, longest day in June |
| 38% | ATREE | 5 | Answer to the riddle "Dressed in summer, naked in winter" |
| 38% | ICED | 4 | With 21-Across, like many rivers in winter |
| 38% | FROSE | 5 | Slushy booze usually consumed in summer |
| 38% | SOLSTICE | 8 | Biannual celebration in Summer and Winter |
| 37% | SKI | 3 | Winter item usually bought in pairs |
| 36% | SOLSTICE | 8 | Shortest day in winter and longest day in summer |
| 36% | LEAPYEAR | 8 | Summer Olympics usually take place in one |
| 36% | STS | 3 | Summer and Winter in Boston, say: Abbr. |
| 35% | MCMXIII | 7 | Year in which the first crossword appeared, on December 21 |
| 35% | SHAD | 4 | Fish usually caught in the winter |
| 35% | LETTERSTOSANTA | 14 | They're usually written in December |
| 35% | ERIE | 4 | Great Lake that's usually the first to freeze in winter |
| 35% | SWEATIERVEST | 12 | A waistcoat worn in summer, compared to one worn in winter? |
| 34% | TBAR | 4 | Transport method usually used in the winter |
| 34% | FIR | 3 | Tree that's usually decorated in December |
| 34% | PTA | 3 | Org. that's usually inactive in the summer |
| 34% | NOG | 3 | Drink made from 6d served usually in December |
| 33% | SKATER | 6 | Performer in both the Winter and Summer Olympics, in different sports |
| 33% | TREE | 4 | What's more naked in the winter than summer |
| 33% | OLYMPIANS | 9 | Those who compete in the Summer and Winter games |
| 33% | SQUASH | 6 | There are summer, winter ones in this gourd family |
| 33% | ATREE | 5 | Answer to the old riddle "What wears more clothing in summer than in winter?" |
| 32% | RAKE | 4 | Yard tool that's usually not necessary in the winter |
| 31% | LOLO | 4 | ___ Jones (American hurdler/bobsledder who competed in both Winter and Summer Olympics) |
| 30% | IAMAROCK | 8 | Song that starts "A winter's day in a deep and dark December" |
| 30% | LOLO | 4 | Hurdler and bobsledder Jones who competed in both the Summer and Winter Olympics |
| 30% | PALACE | 6 | There's a Winter one in St. Petersburg and a Summer one in Beijing |