Hyakunin Isshu 1:
I'm an emperor play-acting as a peasant, but this peasant hut is letting all the rain in, can I stop now?
http://jti.lib.virginia.edu/japanese/hyakunin/noJIS/hyaku1.html

Hyakunin Isshu 2:
Meanwhile in fashion, hillside reports indicate it's time to switch to summer's essential classic white outfit.
http://jti.lib.virginia.edu/japanese/hyakunin/noJIS/hyaku2.html

Hyakunin Isshu 3:
A night spent sleeping alone is indeed long, like the very long and lengthy tail of the (solitary-sleeping) pheasant.
http://jti.lib.virginia.edu/japanese/hyakunin/noJIS/hyaku3.html

Hyakunin Isshu 4:
I must have binoculars to be able to see the snow falling on Mount Fuji from this distance.
http://jti.lib.virginia.edu/japanese/hyakunin/noJIS/hyaku4.html

Hyakunin Isshu 5:
Sarumaru Dayū: The lonesome belling of the deer in the mountains expresses the sadness of autumn.
Deer: Hey, leave me out of this.

Hyakunin Isshu 6:
It's still winter, but I can't stop thinking about Tanabata.

Hyakunin Isshu 7:
The moon in China looks a lot like the moon in Japan.

Hyakunin Isshu 8:
Just because I live in Mount Gloomy doesn't mean that I'm a gloomy fellow.

Hyakunin Isshu 9:
My looks may have gone, but I can still knock off a mean multilayered poem. Good luck unpicking this one.

Hyakunin Isshu 10:
Probably the Heian version of Shinjuku Station is not the best place to meet anyone.

Hyakunin Isshu 11:
Ono no Takamura: Here I go, sailing off into exile.
...
Takamura: I say, you there! Fisherman chappie. Could you pop over to Kyoto and tell my loved ones I won't be back for dinner?

Hyakunin Isshu 12:
Did it hurt when you fell from heaven? Wait, where are you going? I wish the winds would blow closed the path back to heaven, so you'd remain here with me.

Hyakunin Isshu 13:
Behold my river of love flowing downhill.

Hyakunin Isshu 14:
More puns and wordplay. I'm sensing a pattern.

Hyakunin Isshu 15:
I'm doing this for you, you know, out here picking greens and getting snow on my sleeves.

Hyakunin Isshu 16:
Pen me at the pines if you're pining for my painful puns.

Hyakunin Isshu 17:
The river runs red with [checks notes] autumn leaves.

Hyakunin Isshu 18:
Are you that worried about gossip that you won't even come visit my dreams?

Hyakunin Isshu 19:
I have to see you, even if it's only for a short time, like as short as a segment of one of the reeds at Naniwa marsh.

Hyakunin Isshu 20:
Oh buoy, the stakes are high - if I drown myself in the channel, that would marker sad end to my poetic career.

Hyakunin Isshu 21:
You said you'd be here straight away, but I've been waiting all night and now it's dawn.

Hyakunin Isshu 22:
Hey you guys, I found this cool kanji. Combine "mountain" and "wind" and you get "storm."

Hyakunin Isshu 23:
The autumn moon makes me sad, but it's not putting on a show especially for me.

Hyakunin Isshu 24:
I seem to have forgotten to bring an offering for the gods.
[Looks around...]
Er... please accept this gift of autumn leaf scenery.

Hyakunin Isshu 25:
Oh, "sleep-together" vine from "Tryst Hill," if you're true to your name, surely you'll help me get lucky tonight.

Hyakunin Isshu 26:
Hey, autumn leaves, if you could just hold off from falling a bit longer, the emperor will be coming through this area pretty soon now.

Hyakunin Isshu 27:
When did I see you? (I'm not sure I ever did) But I'm crazy about you.

Hyakunin Isshu 28:
Living in the sticks is even worse in winter.

Hyakunin Isshu 29:
Ōshikōchi no Mitsune: Ah, in their self-same whiteness, I cannot tell whether I will pluck chrysanthemum or frost.
Shiki: Yeah, that happened.

Hyakunin Isshu 30:
Mibu no Tadamine: Nothing is more hateful to me than the dawn, since we parted at first light, her face as cold as the lingering moon.
Mibu no Tadamine's coworker: I only asked whether you were a morning person!

Hyakunin Isshu 31:
Early morning moonlight? No, it's snow.

Hyakunin Isshu 32:
Autumn leaves blocking up the river.

Hyakunin Isshu 33:
Hey cherry blossoms, it's a calm and pleasant spring day - why do you have to go scatter yourselves like that?

Hyakunin Isshu 34:
All my old friends are dead and gone - the Takasago pine trees are old but they're not my friends.

Hyakunin Isshu 35:
People change, but the flowers in my hometown still smell the same.

Hyakunin Isshu 36:
Summer nights are so short, it's still evening when dawn breaks - and which cloud is the moon sleeping behind?

Hyakunin Isshu 37:
Dewdrops like scattered jewels.

Hyakunin Isshu 38:
I'm not worried about me since you abandoned me, but you swore a vow on your life. What if something terrible happened to you?

Hyakunin Isshu 39:
Like sparse reeds concealed among bamboo, my secret love... Bewitched, bothered and bamboozled am I.

Hyakunin Isshu 40:
I tried to hide my love, but it showed in my face - to the point that people were grilling me about it.

Hyakunin Isshu 41:
Meanwhile, the rumour mill's in overdrive about my love that's only just begun.

Hyakunin Isshu 42:
We vowed we'd stay together until the waves overwhelmed the hill of pines.
Narrator: They did not stay together.

Hyakunin Isshu 43:
I love you much more now we've spent the night together.

Hyakunin Isshu 44:
If we'd never met, I wouldn't feel bad about being dumped.

Hyakunin Isshu 45:
Kentokukō: Now there's nobody who loves me, will I die sad and alone?
Kentokukō's on-off girlfriend:

Hyakunin Isshu 46:
Love, like a boat without a rudder travelling to destination unknown.

Hyakunin Isshu 47:
Nobody comes to my lonely, overgrown home.
Only autumn.

Hyakunin Isshu 48:
My feelings of love crash and fall like waves against your stony rockface.

Hyakunin Isshu 49:
My passion like the guard fires smouldering through day and burning at night.

Hyakunin Isshu 50:
I thought I'd give up my life to meet you, but I've changed my mind after our night together. Now I want to live forever.

Hyakunin Isshu 51:
My love for you burns like dried mugwort burning on the skin in the traditional form of medicine known as moxibustion.
[note: brush this translation up later]

Hyakunin Isshu 52:
I know the night will come again, but still I hate you, dawn, you scumbag.

Hyakunin Isshu 53:
Do you know how long a night lasts when you spend it alone?

Hyakunin Isshu 54:
You say you'll love me until the end of time, but I doubt you'll keep your promise that long, so I want to die today, unforgotten and happy.

Hyakunin Isshu 55:
This waterfall dried up ages ago, but it's still famous.
Entrance fee: ¥300

Hyakunin Isshu 56:
*On deathbed* Come to me, so I can take our meeting as my last memory of this world.

Hyakunin Isshu 57:
Murasaki Shikibu's friend: Gotta dash. *leaves*
Murasaki Shikibu: But you just got here... *sighs* *writes poem*

Hyakunin Isshu 58:
My heart still flutters for you like bamboo grass blowing in the wind.

Hyakunin Isshu 59:
You said you'd come over, so I stayed up all night waiting until the moon went down.

Hyakunin Isshu 60:
True, my mum's Izumi Shikibu and quite a poet. But she's away now, so can't help me in the poetry competition. Even if she wanted to send a letter I wouldn't let 'er.

Hyakunin Isshu 61:
Someone brings cherry blossoms to Kyoto. (Coals to Newcastle?)

Hyakunin Isshu 62:
Hateful things: Cockcrow imitations, inattentive lovers, liars, you.

Hyakunin Isshu 63:
They won't let me see you again, but I wish I could say farewell face to face.

Hyakunin Isshu 64:
Morning mists lift, uncovering fishing stakes in the shallows of the river.

Hyakunin Isshu 65:
My sleeves drenched with bitter tears, and my reputation. Both ruined.

Hyakunin Isshu 66:
Mountain cherry tree, are you lonely just like me?

Hyakunin Isshu 67:
No, I'm not going to use your arm as a pillow. Brief pleasure, endless gossip.

Hyakunin Isshu 68:
If I must keep living in this hard world, at least I can remember the beauty of tonight's moon.

Hyakunin Isshu 69:
Autumn leaves in the river again (cf. no. 17).

Hyakunin Isshu 70:
I was lonely, so I went out of my hut, but everywhere was just as lonely this autumn evening. (And other Smiths lyrics).

Hyakunin Isshu 71:
This evening, the autumn breeze comes visiting my rice plants and my hut.

Hyakunin Isshu 72:
You show off, splashing around, but I'll stay over here, keeping my sleeves dry.

Hyakunin Isshu 73:
Great view of cherry blossoms on the distant peak, so don't go spoiling it, mist, by rising up and blocking the way.

Hyakunin Isshu 74:
Praying for her to love me only seems to have made matters worse.

Hyakunin Isshu 75:
Promises like sweet dew, dried up in autumn.

Hyakunin Isshu 76:
Fujiwara Tadamichi: Out on the ocean, I mistake great white waves for clouds.
Official: Sir, can I see your boat licence?

Hyakunin Isshu 77:
Our separation is temporary, just as a river runs, is divided by a rock, and comes together again.

Hyakunin Isshu 78:
These plover cries must have woken up the guards at Suma so many times.

Hyakunin Isshu 79:
The wind opens a space in the clouds, and moonlight streams through.

Hyakunin Isshu 80:
My feelings tangled as my morning hair.

Hyakunin Isshu 81:
Turning to where the cuckoo calls, all I see is the lingering moon of morning.

Hyakunin Isshu 82:
Somehow I've lived this long, but I can't hold back the tears.

Hyakunin Isshu 83:
There's no way to escape the world - even here in the mountains, I hear the deer's mournful cries.

Hyakunin Isshu 84:
If I live long enough, I might get nostalgic for this terrible now.

Hyakunin Isshu 85:
Waiting in vain for a lover, a sign of dawn would put me out of my misery, but even the gaps in the shutters are against me.

Hyakunin Isshu 86:
Saigyō: Is it the moon that's got me feeling glum tonight? Moon: Don't blame me, I'm just up here shining.

Hyakunin Isshu 87:
Autumn evening rain still wet on the leaves as mist rises.

Hyakunin Isshu 88:
A night together as short as a piece of reed, but I'll long for him a lifetime.

Hyakunin Isshu 89:
Let my life end now, so I don't reveal my hidden love.

Hyakunin Isshu 90:
Endlessly soaked, fishermen's sleeves remain the same colour (but my sleeves are stained from all the tears you made me cry).

Hyakunin Isshu 91:
Sleeping alone on a chilly night with just the crickets' cries for company.

Hyakunin Isshu 92:
My sleeves like an underwater rock, always wet but nobody sees.

Hyakunin Isshu 93:
If the world could just stay this peaceful. A fisherman tugs his boat into shore with a towrope.

Hyakunin Isshu 94:
Autumn wind in the mountains, the old capital's chill, and the sound of beating cloth.

Hyakunin Isshu 95:
With the ink-black sleeves of a Buddhist priest, I try to protect the people.

Hyakunin Isshu 96:
Blossoms falling like snow, and me falling into old age.

Hyakunin Isshu 97:
I'm on fire for you like the seaweed they burn to make salt.

Hyakunin Isshu 98:
Feels like autumn, but they're still doing summer cleansing rituals in the river.

Hyakunin Isshu 99:
Some people are great, others awful - I waste my time fretting about the world.

Hyakunin Isshu 100:
The palace is all overgrown. Being emperor isn’t what it used to be.

Thanks for reading. I wasn’t sure if I was going to make it all the way through, but I did in the end!

The Hyakunin Isshu is Japan’s most famous selection of poetry, featuring 100 poems in roughly chronological order from the 7th to the 13th century. (Maybe the reason they get gloomier is the decline of the aristocracy over this period).

A few recommendations. This website from the University of Virginia is good for Japanese texts and romaji readings. The translations are not always great or fully reliable, but may be a starting point.
http://jti.lib.virginia.edu/japanese/hyakunin/index.html

With the wordplay and potential for interpretation, there’s no definitive English translation. But Peter MacMillan’s One Hundred Poets, One Poem Each combines poetic skill with solid knowledge of the texts, so very much recommended.
https://www.penguinrandomhouse.com/books/541223/one-hundred-poets-one-poem-each-by-translated-and-edited-by-peter-macmillan/

百人一首新事典is a great book for those who can more or less read Japanese, with contemporary translations, explanations, and manga for each poem. Also, furigana throughout the book.
http://www.zoshindo.co.jp/elementary/256/9784424256014.html

Finally, I enjoyed this app 百人一首読み上げ「わすらもち」, mainly for reading through the whole sequence and (temporarily) memorizing poems. Each one has two English translations (not always brilliant but can be useful).
https://play.google.com/store/apps/details?id=karuta.hpnpwd.wasuramoti&hl=ja