The game of the October 1999 is Silver Jiken. I wanted to write in couple sentences why, but I failed at that miserably and I'd better post a non-structured review of it in order not to overburden this post.
1. Days Innocent [Inspire] VNDB
Mutsuki and Kaede are girl cousins who were very close at childhood friends but have not met for almost 10 years because Kaede illness and transfer. Now Kaede joins other girls in the study and her heart flies to tender their wounds.
Somehow I feel that this game should stay in the list despite quite a big number of H yuri scenes. It's a game of special atmosphere. There is no main character and the story is told from 3rd person perspective. Well, there isn't a story, but rather a collection of event-stories. Map is show and time goes in real time and from time to time character icons show up and there's an even upon clicking. There are five girls. The main line is how weak and lonely Kaede joins the study with other girls and gets supportive with their problems. It's more of a nakige than a yuri work and can be immersive. One playthrough is about 4 hours.
2. Fifth Fifth ～フィフス～ [Rune] VNDB
A mage found a magical girl and decided to raise her. He trains her in Earth, Water, Fire and Air magic with some help. She has the potential to become an angel, demon, or even human. How his treats her will determine what she becomes.
Yet another training SIM. Now the loli version. Actually it's much closer to ADV this time. In ten days there's a devil/angel branch and after 25 days game's over. There are a lot of events scattered around. The amount of text is small. There is no voicing.
3. Gekko 月光 [Uran] VNDB
Hiroshi and Yukiko were going out at school. After graduation Hiroshi went on to university in Tokyo and found a new girlfriend. They meet again in seven years at alumni gathering can't get enough of each other. However Yukiko gets leukemia and gradually weakens day by day.
The game was quite famous in Japan as some critics put it as the nakige of the year 1999 shamelessly pushing Kanon and Kana out. So first chapter is about junior school, second chapter is about new love Izumi and third chapter about Yukiko illness. It's a love triangle and medical nakige mix. I don't appreciate nakige, but medical sickness ones are the worst in my opinion. And only this third sickness story is voiced - that's cheap. There are choices, but they are totally ignored and story just goes in linear manner and it goes to quite crazy level - you may refuse to go to the meeting place with Izumi and you may refuse to date her, but game still would associate you as lovers. Hero is just an indecisive failure. It's probably another work that people either love or hate since evaluations vary from kusoge to kamige.
4. Heart ni Hi o Tsukete... ハートに火をつけて… [Fairytale] VNDB
A beautiful female fighter Ayaka Shimada appeared like a comet in the female fighting sports world and got a nickname "Fighting Goddess". She had a legendary trainer whom she owned her success. Two years later she finally stepped down from the pedestal. New stars show up with the feeling "I want to be as strong as Ayaka!" and it's coach job to fulfill those dreams.
This game is quite ero-centered so I struggled a lot whether block it or not. Training is simplified and battles are fightings are done through cards. But there are quite many H-events in each of the six heroines routes. It's closer to the romance game than a raising SIM, to be honest.
5. Kasumi Yuugi かすみ遊戯 [Purple] VNDB
With the advancing technology, man is able to create realistic man-made humanoids. One variation of such is the virtual brothels, one of which is called Karma. Such places are so expensive that spending one night there costs a month's salary. You as the player of this game, luckily got a freebie guest pass to this virtual brothels. There you meet an overly cute robot called Kasumi, and she is who you will spend your night life with. However, your guest pass can only last for ten visits... Will you be able to stay with Kasumi forever?
There's a good English review on the game.
6. Limit 168 リミット168 [Sweet] VNDB
You have arrived on a mysterious island with no memories. Searching for something that helps you remember, you meet a group of lonely girls...
There's an English review of this game.
7. Maina ~Haja no Ketsumyaku~ 舞菜 ～破邪の血脈～ [Kappa Dou] VNDB
Yoichiro comes from an old religious family, but he's unaware of his roots even though he has a potential. His parents worry about the decline of the clan and they decide to marry him on a talented spiritualist Mai even though he already has a fiance Yuko. The demon is aware of Yoichiro potential and he tempts Yoichiro through his classmate Taeko.
Game is quite dense with H events and story does not really hold much. Even upon choosing an option leading to bad end you can go on from last decision.
8. Niji-iro Season Sarigenaku 虹色シーズン さりげなく [Peach] VNDB
This is the world of sword and magic "Paiona". Three races occupy it.
There is "sword and magic school" in Sao Paolo, the central city of Paonaa. It is a prestigious school where freshmen are only accepted once in three years. At this school "Red Moon Battle" is held every three years when the red moons rise. The winners are recognized as wizards. Four girls participate in the contest to become real witches.
It's something like Sotsugyou ~Graduation~ but in fantasy world. Main hero is actually the teacher that's entrusted with teaching these four heroines. It's a very loose scenario with sudden H events and demon group appearing by the end just to be defeated instantly. The game is actually short and takes one hour to finish. Graphics is the only selling point of the game.
9. Omoide no Photograph 想い出のフォトグラフ [Airyu] VNDB
Yuichiro Ino is a photographer who does not sell well. This time he has to take a job of photographer assistant to get the views of Kyoto. He rides the Shinkansen and gets to Kyoto where he meets four beautiful girls.
ADV with mini-games. Taking pictures is also organized as a minigame. There's no text skip and message speed is not adjustable, so it's a very painful game. Second half is actually about how the hero gets involved in a murder, but the story is sloppy. Period is only three days so development is forced. Enjoy Kyoto views and the girls, quite average game.
10. Prismaticallization プリズマティカリゼーション [Arc System Works] VNDB
Prismaticallization is a dating sim, whose hero is a highschool senior named Shoji. He finds a strange object when he's invited to a summer resort by his classmate Akemi. The object causes him to repeat a day, but seems slightly different.
The same day repeats over and over, but there are some decisions that you can make which affect the next day like the decision whether to keep or leave an item - somewhat like in YU-NO. It's more of an experimental work, but it has much charm about it. Several mysteries remain unsolved. Very few things are explained and players lack information all the time.
11. Psycho Rhythm [Vision] VNDB
Five scientists died in the explosion upon conducting an experiment.
Among them were Samba Hiroshi's parents. He lost parents at the age of 12 and was taken in by the neighboring Imino family. He lost memory and only faintly remembers being in the laboratory just before the tragedy happened. After graduation we started working as assistant detective in the Imino family and the first job is Left Eye case. Over 60 victims were found with their left eye gouged.
Imino family head found the clues to it and was killed while investigating abandoned port warehouse. Samba is set to reveal the conspiracy behind this case and secret ESP's organization that manipulates unknown power with unknown purpose.
Game's based on a very weird engine. The battles in the game are done in turn-based mode with several parameters to take care of - stamina, soul and E.S.P. Each card has attack points, defense points. Upon some condition E.S.P. skills are allowed to use during the attack. As for plot... it's very trashy... I hope the chosen CG alone tells well to what extent.
12. Pure Mind ~Prelude to Harlemblade~ [Giga] VNDB
You play the role of Rian, who lost his memory and was taken care of by a mercenary called Will since 3 years ago. Since then Rian joined Will's mercenary group to work and got pretty popular, especially among girls. Now, Will orders Rian to help stop the war between 2 foreign countries, and through this journey Rian will gradually recover his memory. After Will gives you the task, you have the freedom to choose 1 of the 3 main heroines by finding them in your town. Later, a knight (female) who is one of the 2 warring countries will join you.
There's an English review of this Giga game.
13. Refrain Dream リフレイン･ドリーム [Mu] VNDB
The main character is a graduating high school student.
On Christmas Eve he confesses his feelings to his childhood friend. She passes him the ring saying that she will come to him when he remembers. In a dream a mysterious girl comes to him saying that he should get the paired ring in order to fulfill his hopes.
Paired ring is divided into many pieces and scattered around the world and some pieces are hidden in the world of books. You can gain access to the world of each book by buying the needed book at the antique shop. Different girls need different books. You start with the ability to read three books overnight and that will increase with time. If you choose wrong books, you may fail to meet the girl. There are 8 heroines. So it's a SIM with multiple girls and endings.
14. Renegade Renegade レニゲード [Uran] VNDB
Rail has a faint feeling for his childhood friend Tina.
Tina gets mysterious power and is chosen as chief of the temple because of it. From that day Rail feels that there's impenetrable wall between them. One day Rail meets a woman Luana who is a messenger from the temple and who requests to cooperate to protect Tina against the new king who desires to eradicate the rival in the temple. Rail gathers a team to oppose the king.
Game has no reviews and only after trying it I understood why. No skip. Speed is non-adjustable. Font of previous lines gets blurred all the time. Despite the synopsis there are no RPG elements here. There are a lot of choices, each of 2-3 lines. Battle is shown only to pick which girl to help. So it's an eroge with quite pleasant fantasy story, but horrible system with no options is a huge drawback.
15. Revive... ~Sosei~ REVIVE... ～蘇生～ [Harvest] VNDB
The protagonist of the game, a high-school student, finds himself and other characters (mostly female high school students) trapped in a marine research facility. Exploring the abandoned building, the hero discovers the research staff died under mysterious circumstances. Was this a murder committed by a human being, or some sort of an unknown evil force? The hero does not have much time to think, since whatever took the lives of the scientists also threatens to murder them...
System is akin to prequel Doukoku Soshite with navigation on an isometric map with traps, puzzles and timed sequences. It's definitely much more difficult and fancy than the prequel. There's not much of the story and gameplay does not have fresh feeling anymore, so overall impression is worse than that of the prequel.
16. Silent Duel [Scramble House] VNDB
Jinba high school is a prestigious school where political and business elite children study. A small passenger ship "Silent" is a place for a student party. Hero is preparing the party in the course of his part-time job. The next morning after the party a female teacher is discovered abused and killed. The crew hurried towards the ground, but other incidents happen one by one involving girls assaults. Hero is requested to help the investigation by the teachers.
You move around the boat, get testimonies and investigate. One topic of conversation takes 10 minutes and time is limited. The theme of the work is "fight to protect" and not only against the criminals but also from self. There are five heroines. Graphics is ok and there's a solid feeling from the game, but it has specific content.
17. Silver Jiken シルバー事件 [Grasshopper Manufacture & Active Gaming Media Inc.] VNDB
1999 - the "24 Wards". A string of mysterious serial killings plagues the city. The detectives of the 24 Wards Heinous Crimes Unit have their eyes on one man: Kamui Uehara, legendary serial killer and assassin of a number of government officials 20 years prior in the now-famous "Silver Case". However, nobody knows who - or what - Kamui really is. Has he really returned? Who is this infamous serial killer?
Game is localized and has dozens of reviews.
18. School Quest ~Heroine~ スクール・クエスト ～ヒロイン～ [Hyperspace] VNDB
Let's fall in love with three heroines at school and around the town.
School - part-time job and lots of schedule management. Raise the three parameters - money, strength, experience - and go on a date. Girls have two parameters - experience and the level they like you. Moving around town is as if came down from RPGmaker, totally ugly and by squares. There's no story besides making it with the girl, but since it's a SIM, it should stay.
19. Sta★Gra -Star Graduation- スタ★グラ -Star Graduation- [Active Soft] VNDB
2027. Aliens came to the Earth and for a year a group of them will study as international students for a year. They aren't much different from humans apart of some features like wings and tails - and they have special abilities. Main hero is student council chairman and he needs to help them socialize.
Another SIM. There is a set of parameters like curiosity, intelligence, physical strength. There are five heroines. Hero needs to organize his schedule for each week. On weekends the only option is to rest or to go on a part-time job. There are a lot of fixed events like sports tournaments or national holidays, so it gets repetitive on consequential playthroughs. Basically we only need to raise specific parameter so specific value and one of girls will automatically take the bait. Since heroines are aliens, they follow some archetype - cat, maid, angel, raccoon, fish. Otherwise nothing out of ordinary.
20. The Ren'ai Simulation ~Natsuiro Celebration~ THE 恋愛シュミレーション～夏色セレブレーション～ [HuneX] VNDB
You're a high school student enyoing summer with your best friend Kimi. One day of August, she receives a call from her father, telling her to go home in 21 days. You then start enjoying those last days together...
There are 10 heroines. And you create them yourself... there are tools for it. Apart of that there are parameters and lots of actions to fill the schedule. So it's a very basic level SIM with ability to create own event situations.
21. Zero Jikan e... ゼロ時間へ・・・ [Easy Mode] VNDB
A gigantic meteorite will fall on the Earth in 3 days destroying it forever. At this time one amateur astronomer's photo of the comet tail initiated a series of full-scale riots and mayhem. How will you live three last days in such a world?
Another end of the world story. Command selection ADV, but creator tried to make it as user-friendly and speedy as possible. The is some gunpowder in some of heroines stories, but they are too short to have an impact. There are some 20 endings. Well, there is some unique atmosphere of lawless ruined Tokyo, so might be to someone's taste.
22. Zoku Mikagura Shoujo Tanteidan ~Kanketsuhen~ 続・御神楽少女探偵団～完結編～ [Nude Maker & Human Club] VNDB
Zoku Mikagura Shoujo Tanteidan - Kanketsuhen is the sequel that finishes the story of Mikagura Shoujo Tanteidan. The game features some action sequences in which the player has to press a directional button or an action button to pass it and advance in the game, if the player fails he will have to repeat the action sequence again.
The only new feature is mentioned in the synopsis. There quite a lot of interesting and fun cases here as well, but the impact is much smaller than that of the prequel. So if you like Taisho era atmospheric detective stories, nothing should stop you from playing it. Opening is pretty much the same as that of the prequel, just some eyes changed.