Timeline

Please note this timeline is taken from my point-of-view from manga and anime related elements respectfully. I've tried to keep many events focusing on Krillin mostly, but many other events have been included. I will try to include Dragonball GT and also any movie related elements, but I do not consider the movies to be entirely true. Most of these year dates are thanks to Dragonball Daizenshuu and the DBGT Perfect File books. Other sources come from the manga and years I've counted out myself.

732 Age- Vegeta is born.
733 Age- Bulma, Yamcha, and Tien are born.
736 Age- Krillin is born.
737 Age- Goku and Chi-Chi are born, where Goku gets sent to Earth as an infant baby right before Frieza blows up Planet Vegeta. Broly, if considered to be an sync with the regular anime, was also born as well. Nappa, Vegeta, Raditz, Goku, and Tarble are the only Saiyans to survive, unless you count Broly and his father.
740 Age- Krillin starts training at the Orin Temple at the age of four.

749 Age September- Goku meets Yamcha, Bulma, Master Roshi, Oolong, Pilaf, and Krillin. Krillin and Goku do eight long month training sessions together until the 21st World Martial Arts Tournament.
750 Age- Krillin finishes third place in the 21st World Martial Arts Tournament, while Goku takes second plage. Goku starts to face off against the Red Ribbon Army including General Tao and Krillin fights against General Blue. Goku evetually defeats the Red Ribbon Army and sees Grandpa Gohan, while Krillin continues his training with Master Roshi.
753 Age- Krillin is killed after the 22nd World Martial Arts Tournament and starts the events of the King Piccolo saga. Krillin is later revived with the Dragonballs for the first time.
757 Age- Gohan and Videl are born. (End of DB.)

761 Age (Late)- Raditz arrives on Earth and kidnaps Gohan, while we learn Goku is a Saiyan. (Start of DBZ.) Gohan's training starts with Piccolo.
762 Age (Early)- Krillin starts his training at Kami's Lookout and travels to the old Planet Vegeta, where he is easily killed by two weak Saiyans. After realizing it was only his spirit that went, Krillin trains and grows to become as strong as Raditz was when he first arrived on Earth.
762 (Late) Age- After traveling to Namek after the battle with Vegeta on Earth, Krillin meets Dende and has some (if not all) of his hidden potiental unlocked on Namek by Guru. Krillin is killed by Frieza in December and Goku transforms into a Super Saiyan for the first time. (What a wonderful Christmas present huh? xD) Krillin is later revived the following year (763 Age).
764-766 Ages- Trunks warns the Z Fighters of the approaching Androids and they all train, including Krillin. The 24th World Martial Arts Tournament takes place during this time, though Hercule wins. In December in the two alternate timelines, Goku dies of the heart virus.
767 Age- The Androids are woken up and Cell is defeated by Gohan. In the alternate timelines, all of the Z Fighters die on May 24th of this year. Goku survives his heart virus but he is killed by Cell and choses not to be revived by the Namekian Dragonballs and Goku's funeral is held. If considered true, Bojack is released and Gohan defeats him.
770-773 Ages- Krillin and Android 18 are married (770) and Marron is born (771).
774 Age- Gohan enters high school and Krillin decides to enter the World Martial Arts Tournament, where we first see he has his hair grown out. Majin Buu released and the final big battles begin for the sake of Earth and the fate of the universe. Goku defeats Majin Buu with a Spirit Bomb.

776-794 Ages- Gohan and Videl are married, while Pan and Bra (Bulla) are born between these years. Pan enters the 28th World Martial Arts Tournament at age of four and Goku begins to train Uub (end of DBZ). In the alternate timelines, Gohan is killed in 780. Trunks is killed by Cell in one of the alternate timelines and takes the time machine, while Trunks in 'main alternate timeline' easily defeats Cell. Goku is wished into a child again by Pilaf (start of DBGT).
795 Age- Krillin is killed by Android 17 and Omega Shenron is defeated, while the Dragonballs are no longer allowed use on Earth. Goku has one last "fight" against Krillin and leaves with Shenron.
After 795 Age- More descedents are born from Vegeta's and Goku's respectful families and by 896, Pan is over 100 years old and she sees Goku grown back up into a man. (End of DBGT.)