24 November: The USS Enterprise makes contact with the planet Equus, in the region of Equestria, while tracking down a suspect in a murder. Commander Data meets with Orion Shadow, whose wife, Raven, was taken by a member of a species known as an allasomorph. The transport ship Raven is on is captured by the Borg, and Raven is assimilated into the Collective. A rescue by Orion and the members of the Enterprise crew is successful in retrieving Raven and removing a large portion of the Borg technology. They then return home to Equestria.
03 January: Princesses Celestia, Luna, Twilight, and Cadance are briefed by Orion on his and Raven's adventures and contact with the humanoid races of the Federation. All agree such information should be kept highly secret, and not divulged to the general population of Equestria.
24 November: Raven's Borg implants reactivate, and she accidentally injects Orion with Borg nanoprobes. Realizing time is of the essence, they enlist the help of Discord (known to the Federation as Q) to return them to the Enterprise to once again fight off the Borg attempts at assimilation. Afterwards, agreeing that their appearance would be upsetting to the citizens of Equestria, Orion and Raven agree to a posting aboard the Enterprise for familiarization and basic training prior to being assigned to a starship.
26 August: Orion and Raven are present for the events surrounding Picard, Kirk, and the destruction of the Enterprise-D, as seen in Star Trek: Generations. Both ponies return to Equestria to make final preparations as they await the completion of their own ship.
24 September: As part of a pilot program by Starfleet to welcome their new equine members, Orion is given command of the Shadowfall, a Miranda-class vessel used primarily for scientific and diplomatic missions.
15 October: Archaeologists from Luna University return from their expedition in the Badlands, having discovered scales from the original sirens that once inhabited the planet prior to their banishment by Star Swirl the Bearded. At the decree of Princess Luna, one scale from each siren is to be preserved in the royal vaults while the rest are free for public display.
23 November: The USS Shadowfall is present in the battle with the Borg that leads to a major temporal shift, seen in Star Trek: First Contact. Given his experience in matters relating to the alteration of time, Picard recruits Orion’s help.
14 April: The Shadowfall is one of the 627 ships that Benjamin Sisko recruited to help in a battle to retake Deep Space Nine.
17 June: Orion and Raven return to Equestria with a Federation delegation, seeking to establish peaceful relations with the Sovereign Diarchy of Equestria, speaking for the planet Equus. They are received following the Summer Sun Celebration by Princess Celestia and her sister, Princess Luna. Captain Jean-Luc Picard is selected as one of the dignitaries for this event, at the request of Orion, in gratitude for all of his assistance.
01 September: Formal talks are begun to establish relations between Equus and the Federation.
14 November: In a timeline created by Discord, Orion is forced to finally participate in the Dominion War properly. He becomes so exhausted by the fight that he develops a weapon that would turn the Shadowfall into a weapon of mass destruction, but he is sent forwards in time by 29 years before it can be deployed.
24 September: Orion's five-year mission aboard the Shadowfall is complete. He is reassigned as official Equestrian advisor to the Federation and is posted to Canterlot. He opts to maintain his home in Ponyville, commuting as his duties require.
01 March: At the first summit on humanoid-equinoid relations, Orion relates his difficulties serving as an equine aboard a starship populated with humans and human-like beings. Speculation begins through the scientific community if a being could be born with the traits of an Equestrian pony and an Earth human. Sanctioned by Princess Celestia and the chief of staff at Starfleet Medical, work begins on a super-secret project.
17 June: Equus is accepted into the United Federation of Planets, with its chief point of rule resting with the Sovereign Diarchy of Equestria, by mutual agreement of all sentient species upon the planet. Technological and thaumaturgical information is now able to be freely exchanged, greatly advancing the super-secret project begun earlier in the year.
04 September: Princess Luna presents the siren scales to the team working on the super-secret project, asking if the DNA from them can be extracted and used as part of the experiment. The scientists agree to try.
14 February: The “Hearts and Hooves Breakthrough” is announced privately by the scientists working on the super- secret project, with the announcement that a stable matrix has been produced to allow the combination of human and equine DNA strands into one cohesive unit. It is also announced that the siren DNA has been extracted successfully, and is also compatible with the biological matrix.
07 March: The Royal Sisters, in conjunction with Starfleet Medical, approve the production of the first ever artificial ovums containing humanoid and equinoid DNA. The samples are not meant to be fertilized, but studies to see how long they will remain viable and whether the biological matrix combining the two different DNA strands doesn't degrade.
30 September: A special summit is held at Canterlot Castle, at the request of the Royal Sisters. Attending this summit are Orion and Raven Shadow, Twilight Sparkle, and Emerald Wave. It is announced that the process of creating human/equine hybrids is now ready for the final phase: the in-vitro fertilization of the synthetic ovums containing the DNA of the parents and an anonymous human donor. Those in attendance are asked to provide DNA samples, all readily comply.
2 October: Onyx, King of the changelings, learns of the Federation's cloning program with the ponies of Equestria and Orion's clone in particular. He begins planning how to use it to his advantage.
11 October: The changelings and the Romulans have First Contact when a Romulan scout ship lands outside the changeling hives.
14 December: Orion Shadow officially retires from Starfleet, and is granted the title of civilian advisor to the Royal Sisters on interstellar affairs.
27 April: Fawkes and Philomena Shimmer are killed by a runaway cart in Ponyville. Sunset is declared an orphan and, with no other family able to take her in, enters the foster foal program, which ships her to her first foster family in Dodge Junction.
16 July: Sunset is returned to live with another foster family in Ponyville, not adapting well to life with earth ponies in Dodge Junction.
01 August: All of the human girls and Sunset are enrolled in school in Ponyvile. Dustin is granted permission to attend public school in Canterlot, despite objections from Princess Luna, who fears young Dustin might become a target for the changelings.
02 August: At Sunset's request, Emerald changes Sunset to human form, to see if it's really what she wants to become. The spell is designed to last for one month.
01 September: Sunset agrees that being human is indeed what she wants in life, and the spell is made permanent. Orion and Raven, having heard of her plight as an orphan, begin the process to legally adopt Sunset. Later that same day, the first manifestations of magical powers were demonstrated by Sunset, Gemini, Raven, Emerald, Twilight, Adagio, Sonata, and Aria as they defended the town from a robotic experiment gone wrong. Later that day, Adagio, Aria, and Sonata took merpony form for the first time when they went swimming in a nearby lake.
2 May: The Romulan Senate learn of a star going supernova that poses a threat to the entire galaxy. They task Ambassador Spock to pilot a specialized ship, equipped with red matter, with the intent to engulf the supernova by creating an artificial black hole.
12 May: Changeling infiltrators, posing as ordinary foals, attempt to abduct Dustin while he was on his way to school. An alert off-duty royal guard, passing near the school, heard Dustin's shouts and, with assistance from the others with him, managed to prevent the attempt. The changeling agents escaped.
13 May: Princess Luna has Dustin withdrawn from public school and has tutors provide instruction in the castle, along with the foals of the servants to provide Dustin with playmates.
23 May: The supernova reaches Romulus, destroying the planet.
20 June: Spock launches red matter into the supernova, creating the artificial black hole and neutralizing the star. The resulting black hole consumes his ship along with the nearby Romulan mining vessel Narada commanded by Nero, sending them back in time to 2233, creating an alternate timeline in the process.
7 May: While touring the Canterlot Botanical Garden, one of Dustin's friends was stung by a tentacle of nasty nettles. Dustin's magical powers manifested that day when he gathered healing herbs and, combining them and the healing magic in his hands, slowed the spread of the poison until his friend could receive proper medical attention.
6 August: Sunset opens an informal “counseling booth” at school, encouraging her fellow students to come and talk to her about their problems. She has great success in getting students that wouldn't ordinarily open up to the staff talk about their deepest problems and fears.
1 October: At the request of Princess Celestia, the hybrid students are given a battery of tests to determine their intellectual and creative aptitudes. All of them score in the exceptionally-high to genius levels. Sunset, given the same tests, scores at the exceptionally-high level as well. As a result, she is mixed into the same classes as her hybrid counterparts.
5 March: Princess Celestia urges Dustin to take the MCATs due to his high aptitude for medicine. He scores a perfect 528, and earns high marks for the written essay portion of the exam. Princess Luna sees these scores and enrolls him in Canterlot Royal Medical College upon completing his secondary-school studies.
31 October: During a Nightmare Night party, Adagio, Sonata, and Aria revealed their talent for singing. Along with the other five girls, and dubbing themselves The Rubies, they performed so well that they hypnotized their audience during their song.
20 May: Dustin Hoofer, M.D., completes his internship at Royal Canterlot Hospital, the quickest internship of any student prior. Seeing very little opportunity for him to advance his medical studies in Equestria, he submits a formal petition to Princesses Celestia and Luna to be allowed to continue his studies on a planet called Earth. The princesses reluctantly agree, and Doctor Hoofer is accepted into the residency program at the Mayo Clinic, Rochester, Minnesota, Earth. He departs with little fanfare on a passing transport.
27 November: Gemini and the others all come to the same agreement: to better further their studies, they will need to enroll in Starfleet Academy due to the limitations Equestria has in furthering their educations.
30 November: The eight are taken aboard the Enterprise-E for their trip to Starfleet Academy. By special dispensation from Starfleet, all entrance examinations are conducted during the voyage.
8 December: Gem and friends are assigned to the cadet class as first-year cadets in Starfleet Academy, Class of 2401.
20 June: The USS Endeavour, a refitted version of the USS Shadowfall, takes off on her maiden voyage, with Gemini Shadow leading the crew of Earth humans, Equestrian humans, and a small assortment of other species. The total crew complement is 36. During their first mission, they travel to a planet shrouded in everlasting night, and do battle with Nightmare Moon, who has taken over one of the planet's local rulers.
26 July: The Endeavour encounters a time eddy, transporting it back to the days of Kirk's Enterprise, specifically the Organian mission. Captain and Commander Shadow with Lieutenant Commander Sparkle beam down to assist in the negotiations.
2 August: The Endeavour finds the lost USS Magellan, which has been infested with Regulan bloodworms. Captain Shadow manages to be bitten by one when it hides inside her glove, and is saved via Dustin Hoofer’s unique medical treatment methods.
10 August: Pavel Chekov, now an Ambassador of the Federation, joins the Endeavour to begin negotiations with the inhabitants of the planet Eurybdis-47, only to find that Mr. Chekov has turned traitor, seeking to use the Endeavour as an instrument of war for revenge against his former captors.
7 September: A transporter malfunction sends an away team consisting of Captain Shadow, Lieutenant Commander Sparkle, Lieutenant Dazzle, and Lieutenant Shimmer into a parallel reality, leaving evil equivalents in their place. Hours later, Gem is put to a test by Discord to see if she really does follow in her father’s hoof steps when faced with an impossible choice.
14 September: While inside a J-class nebula gathering deuterium, Emerald Wave becomes the host body of a being from the Sen-Siddarian race.
16 September: The Endeavour returns to its spiritual home of Equestria to begin negotiations with the Romulans while Gem, Raven, and Sunset deal with the fallout of their parents’ deaths by Romulan hands.
28 October: The Endeavour meets the crew of the USS Voyager, who have been shifted in time by 30 years.
5 January: Captain Shadow is temporarily removed from command by Admiral Nechayev, and is replaced by Abacus Cinch, CO of the USS Cairo. By order of Capt. Alan Brown, Gem and two other members of her crew are captured by the Cardassians and tortured while Commander Raven launches a mutiny and a subsequent rescue mission.
20 January: The Borg return to Wolf 359 and capture Captain Shadow, turning her into their queen, but the attempted takeover of the ship and its crew fails when a newly-developed weapon, the Orbital Friendship Cannon, is deployed.
20 June: On the 1-year anniversary of their travels, the Endeavour is besieged by changelings as Queen Chrysalis launches an attack on the vessel. Ensign Milo Iscariot is revealed to be an agent of Chrysalis, and the crew are taken to Starbase 421 as hostages, though they are rescued by another changeling queen, Calyx.
4 July: A strange transmission purporting to be from Captain Gemini some two hundred years previously is investigated and revealed to be an elaborate hoax perpetrated by a race of snake-like creatures intent on using the Endeavour as a breeding colony.
9 July: The deceased parents of Captain Gemini and Commander Raven are temporarily brought back to life, though the puppet bodies they inhabit fall apart quickly.
14 August: An enigmatic traveler called the Doctor arrives to assist the crew in stopping the Borg and a similar race, the Cybermen, from conquering the universe. This eventually results in the Endeavour crew forming a temporary alliance with the Borg, as it turns out that without their help, the universe would eventually fall to the Cybermen.
8 September: The Mirror duplicate of Captain Gemini attempts to murder her Prime counterpart in a misguided plan to use the Endeavour as a stepping stone to become Empress of the Federation.
15 September: Following the events of Sept. 8th, Admiral Nechayev orders Captain Gemini to assist her in exterminating the Terran and Equestrian Solar Empires, citing a perceived threat to the Federation. Gem refuses, and sneaks into the Mirror Universe to warn Empress Celestia of what is coming.
24 December: On the planet Chiron Beta Prime, Dustin Hoofer delivers gifts to the native people, a race of humanoid reindeer.