Toronto-born Omar Khadr pleaded guilty to five charges: murder, attempted murder, conspiring with terrorists, spying and providing material support to terrorists. The plea came as part of a deal with prosecutors at the U.S. military commission at Guantanamo Bay, Cuba.

It was understood the deal would let him serve the first year of his eight-year sentence in U.S. custody in Cuba, and then move on to custody in Canada if U.S. and Canadian authorities agreed.

Khadr admitted in the military court to throwing a grenade that killed U.S. Sgt. 1st Class Christopher Speer during a firefight in Afghanistan in 2002. When asked if he conspired with Osama bin Laden and al-Qaeda, Khadr also answered "yes."

Here are the major developments in Khadr's trial:

Nov. 1

CBC News reports that Khadr would spend his remaining year at Guantanamo Bay in the highest-security section of the detention facility, and then be eligible for transfer to Canada, where he would serve out the remainder of his five-year sentence.

Oct. 31

A U.S. military jury in Guantanamo Bay says Khadr should serve 40 years in prison for war crimes, a symbolic decision because a pre-trial plea deal caps his sentence at eight years.

Oct. 30

The military jury hears closing arguments in the case. The lead prosecutor calls Khadr "a terrorist and murderer" who should serve 25 years in prison.

Defence lawyer Lt.-Col. Jon Jackson says his client was coerced into going to Afghanistan by his father and deserves "not a second chance" but a "first chance," because Khadr has never had that before. Jackson does not make a recommendation in terms of number of years for a prison sentence, but instead asks the the jury to consider the time Khadr has already spent in detention.

Oct. 29

Khadr's sentencing hearing adjourns unexpectedly after an hour. Defence lawyers use the time to enter into evidence an unsworn statement by Khadr in which he admits he initially lied to U.S. interrogators in Afghanistan after his capture.

Oct. 28

Khadr apologizes to Speer's widow, saying that he is sorry for the pain he caused the American soldier's family. "I wish I could do something that would take away your pain," he says during his most extensive comments since his capture.

Tabitha Speer had testified earlier in the day that her husband was a "most generous, loving" husband before he was murdered by Khadr.

Oct. 27

A forensic psychiatrist testifies for the prosecution at the sentencing hearing. Dr. Michael Welner says that Khadr is likely to return to a jihadist environment after he is freed from detention unless he is first deradicalized.

Later in the day, Khadr's lawyers try to discredit Welner's testimony. They suggest the psychiatrist's knowledge of radical jihad behaviour is based primarily on the controversial work of a third-party psychologist rather than his direct assessment of Khadr.

Oct. 26

A hearing to determine Khadr's sentence begins. Military judge Col. Patrick Parrish urges the seven jurors who will recommend Khadr's sentence to "keep an open mind," reminding them of their "grave responsibility … to exercise with wide discretion."

An agreed statement of facts is read aloud in the courtroom by the U.S. prosecutor. It states that Khadr threw the grenade after a firefight with U.S. soldiers had ended and did so "with the specific intent of killing or injuring as many Americans as he could."

Oct. 25

Khadr pleads guilty to all five charges as part of a plea deal. Parrish accepts Khadr's pleas and tells him he will be eligible to apply for transfer to a Canadian prison after serving one year of his sentence in U.S. custody. The plea deal will see Khadr serve eight years in prison total, according to reports.

Oct. 21

More details emerge about a possible plea bargain in Khadr's case, as reports circulate that U.S. Secretary of State Hillary Clinton is personally involved in the negotiations.

Oct. 14

CBC News confirms there are talks between the U.S. government and Khadr's defence team aimed at reaching a plea deal ahead of the resumption of his war-crimes trial at Guantanamo Bay, Cuba.

Aug. 13

The military judge calls for the trial to be delayed by at least 30 days while defence lawyer Lt.-Col. Jon Jackson convalesces. Jackson, who had gall bladder surgery six weeks ago, is to be airlifted to a U.S. medical facility after collapsing in court the previous day.

Aug. 12

Opening statements are made. The defence says Khadr didn't throw the grenade that killed Speer and there is no forensic evidence to prove he did.

The prosecution paints a starkly different picture, saying that Khadr confessed freely to his alleged crimes and was "a terrorist trained by al-Qaeda." The defence claims the confession was coerced. The prosecution also shows video that it alleges shows Khadr planting improvised explosive devices.

Aug. 10-11

The seven-member jury — four male and three female U.S. military officers — is selected for Khadr's trial. Their identities will be shielded. At least five of the jurors will have to agree that Khadr is guilty to secure a conviction.

Aug. 9

Khadr formally pleads not guilty to five war crimes charges during a pretrial hearing in a Guantanamo Bay courtroom.

During the session, the judge says he will allow into evidence an apparent confession Khadr made while in custody, rejecting defence arguments that Khadr's statements were the product of torture and could not be used against him.

More: The case, the allegations and Khadr's family history