1770 The Turk, A Fraud
The first automaton chess player was called The Turk, it was constructed in 1770 by Wolfgang von Kempelen. The Turk toured Europe and famously played Napoleon of France. Unfortunately the Turk was a fraud, a strong player was concealed in the inside of the machine. Sadly the Turk was destroyed by a fire in 1854.
1951 Alan Turing Paper based program
The father of AI Alan Turing created a paper based algorithm to play chess. A recorded game took place in 1952, Turing never had a computer powerful enough to run the program so he had to do the calculations by hand and the game took several hours to complete. Unfortunately the program lost, but it did play a reasonable game considering.
First Chess Program, but incomplete, Dietrich Prinz 1952
Dietrich Prinz who learned programming from the seminars by Alan Turing. Independently of Turing, Prinz wrote a computer program which concentrated on the end game (few pieces) and was able to solve a simple mate in 2.
1957 First complete chess program Alex Bernstein
The world had to wait a further 5 years until a full chess playing program was developed. Running on a IBM 704 computer, Alex Bernstein was the programmer. The machine took around 8 minutes to make a move but alas I cannot find any example games of chess and the program did not appear to have a name. All I could find is some video of the machine playing its creator.
1962 MIT Chess program beats amateur Kotok-McCarthy
MIT became the hotbed of chess research with several teams making progress in the field of computing and chess programming. The Kotok and McCarthy team made progress to the point a computer could beat an amateur player.
1967 MIT Richard Greenblatt achieves elo 1400
Richard Greenblatt made further advances with his program Mac Hack which ran on a PDP-6 computer and played in human chess tournaments to achieve a rating of 1400, it was the first program to beat a human player in tournament play. By 1977 the program had reached an elo of 2100 and played 3 games against Bobby Fischer who beat it easily, see the example game.
1968 IM David Levy bets no computer could beat him in the next decade
A famous chapter in computer chess was the bet International Master David Levy made in 1968 that no computer would beat him in the next decade. The bet was settled in 1978 when Levy beat Chess 4.7 in a match to win the bet. The example game is the first game in that match that Levy won with the black pieces. He won the match fairly easily only losing the one game.
1977 First microcomputer chess playing machines Chess Challenger and Boris
The late 1970's saw the development of dedicated commercial chess playing computers, a number of companies started to produce chess computers, Fidelity and Saitek among them.
1978 Levy wins his bet beating Chess 4.7 4.5-1.5
As mentioned above Levy won his bet in 1978, included here is his only loss.
1981 Cray Blitz performance rating 2258
Cray Blitz was the first computer to win a state championship, it won the Mississippi State Championship 5-0 and achieved a performance rating of 2258. The example game is the win against Joe Sentef rated 2262.
1982 Belle earns Master title
Chess computer Belle competed in the 1983 US Open, achieving a performance rating of 2363. I couldn't find any games from that tournament but the example game sees Belle defeat Cray Blitz with the black pieces.
1988 GM Arnold Denker defeated by HiTech
Arnold Denker was the first Grandmaster to lose to a computer in a match, the link below is a short report on the match with a couple of interesting photos of Denker and the computer itself.
1989 Deep Thought loses against Gary Kasparov
Gary Kasparov won a 2 game match against Deep Thought in 1989 which was the start of series of matches where computers were trying to beat the current World Champion.
1997 Deep Blue beats Gary Kasparov
Up until this match Kasparov had been holding back the tide of computer chess progression for humanity, but unfortunately he was defeated in 1989 in a rematch against the IBM monster Deep Blue, a computer which he had defeated 4-2 in 1996. The match was fairly controversial as Kasparov accused IBM of cheating. Kasparov was ready to challenge the computer to a rematch but alas that never materialised. If you are interested there is a documentary about this match called "Game Over: Kasparov and the machine".
2005 Hydra crushes English GM Michael Adams 5.5 - 0.5
Humanity was further humbled when English Grandmaster and former world champion contender Michael Adams was thrashed by Hydra, obtaining just a single draw in their 6 game match.
2006 Kramnik defeated 4-2 by Deep Fritz
Humanities grasp on chess was finally released when GM Vladimir Kramnik lost to a computer program running on ordinary hardware that anyone could purchase in the high street. Deep Fritz won the match 4-2 though it was helped by a blunder.
From this point on further development meant that a human will never be able to win a game against a computer, the best result you could possibly hope for is a draw. Interestingly in old times strong players used to give odds to opponents and this may well be a feature that we may see in future man v machine chess matches.