The Hoyle series is one of the hardest, if not the hardest, series to properly cover, simply because there are so many releases (many by the same name), because the games were hardly advertised, and are barely covered on the internet. However, after a lot of research, this is what we have found.
The first Hoyle titles (1989-1993)
The first Hoyle game, Hoyle: Official Book of Games: Volume 1, designed by Warren Schwader, was released with EGA graphics and the SCI engine in 1989. It contains six different games: Cribbage, Crazy 8's, Gin Rummy, Hearts, Klondike Solitaire and Old Maid. Although it was the first Hoyle game, it wasn't Warren's first game design involving cards - as the first hired programmer of Sierra On-Line (then still On-Line Systems) he also designed Hi-Res Cribbage in 1980.
Hoyle Official Book of Games, Volume 2: Solitaire, also designed by Warren and released in 1990, offers a whopping 28 varieties of Solitaire games. Hoyle Official Book of Games, Volume 3: Great Board Games, released in 1991, was the first Hoyle title with VGA graphics (though also with EGA) and without the involvement of Warren - it was designed by Marti and Bridget McKenna. The game, aimed at younger audiences, contains Backgammon, Checkers, Pachisi, Yacht, Dominoes and Snakes & Ladders.
In 1993 the first Hoyle game was remade with VGA graphics and an additional two games: Bridge and Euchre. Titled Hoyle Classic Card Games, it was Warren's last game designed at Sierra, as well as the last Hoyle game featuring Sierra characters as opponents.
Revival of the Hoyle series (1995-1998)
Hoyle Classic Games, also referred to as Hoyle 5, was the first follow-up to the classic Hoyle titles, and the first on CD-ROM. Released in the fall of 1995, it featured 10 games: Bridge, Poker, Hearts, Cribbage, Backgammon, Checkers, Old Maid, Crazy Eights, Gin and Solitaire, so a mix of both the classic card and board games, as well as featuring Poker for the very first time. Sierra characters were no longer included as opponents from here on.
Also spin-offs were made, containing one or more games from Hoyle Classic Games and released as Sierra Originals. These are Hoyle Children Collection and Hoyle Bridge. Hoyle Children Collection contains only Checkers, Old Maid, and Crazy Eights. Hoyle Bridge only contains the Bridge game. Also Hoyle Official Book of Games, Volume 3 was re-released as a Sierra Original under the title Hoyle Classic Board Games.
In the summer of 1996, the series continued with the release of Hoyle Solitaire and Hoyle Blackjack. And in December 1996, Hoyle Casino was released. Hoyle Poker, originally planned for release before Christmas 1996, had a delay and was released in April 1997.
From 1997 on, Hoyle games became less and less advertised, even barely being covered in Sierra's own InterAction Magazines. As mentioned before, Hoyle Poker was released in April. Also in 1997, Hoyle Casino was re-released - same game, different box. And in November 1997, both Hoyle Classic Board Games and Hoyle Classic Card Games were released.
Hoyle Classic Board games includes 10 games (including Backgammon, Dominoes, Chinese Checkers and Battling Ships) plus 2 bonus card games. In addition the box apparently also included Hoyle Blackjack (stock leftovers perhaps?).
In 1998 the last Hoyle games prior to the Cendant merger were released. Notice that the ESRB rating changed at this point to E (Everyone) from K-A (Kids to Adults). Also notice the similarities in the new cover design, from the bulky header to the slogan "Family Fun For Over 200 Years." These are the last Hoyle releases with the classic Sierra logo. After the merger, several of these games were re-released, apparently repackaged stock leftovers. The original white boxes are apparently very hard to find.
These games are Hoyle Battling Ships and War, Hoyle Bridge & Euchre, Hoyle Hearts & Spades, Hoyle Solitaire, Hoyle Classic Games and Hoyle Poker. Hoyle Solitaire and Hoyle Classic Games are apparently re-releases of the 1995 and 1996 games.
Sierra Attractions Hoyle titles (1998-2002)
Sierra was not yet done with re-releasing existing games in new packaging.