10/24/2026
Note: Celebration of Life will be at the Legion November 8th from 2:00-5:00pm.
Obituary for Bob Critchley
Brian Cyril “Bob” Critchley
Brian Cyril “Bob” Critchley passed away on the morning of October 21, 2026, at the age of 91. A Leaf fan at heart to the very end, he remained devoted to the game, the team, and the friendships sport brought into his life.
Bob was born in Sheffield, England, in 1935 and grew up during the hardships of the Second World War. His childhood memories included blackouts, gas masks at school, and nights spent in bomb shelters. Unless there was action overhead, that is. On those occasions, his uncle Percy would let him emerge and watch the anti-aircraft fire light up the night sky.
A brief military career ended with a medical discharge following a motorcycle accident. In 1967, Bob emigrated to Canada, and in 1977 he made Erin his home. He worked as a hammer man and saw smith and became an active member of the Erin Legion and the wider community, where he formed many lasting friendships.
Sport was woven throughout Bob's life. He had a professional-level soccer career in England, but hockey became his greatest passion. Remarkably, he learned to skate at 37 and didn't begin playing hockey until he was 41. Through his love of the game, he was eventually afforded the opportunity to play with the Leafs Oldtimers. To Bob, that made him a Leaf.
At an age when many people slow down, Bob embraced new challenges, taking up skiing, baseball, and tennis. He was particularly proud of recording a 170 finish in darts, although he would insist he could have done it in his sleep during his prime, if only Yorkshire dartboards had included trebles.
Whether he won or lost never mattered much. The real joy came from the camaraderie, the competition, and the friendships forged through sport, both playing and coaching.
Those who knew Bob also knew his unique way of speaking. Friends in England claimed he had lost his accent; friends in Canada sometimes wondered if he was speaking English at all. Either way, he was never short of stories, opinions, or memorable sayings. His favourite expression, offered to anyone going through a difficult time, was: "Could have been worse, could have been me." It was his way of bringing perspective and a smile when one was needed most - This time, it was the worst. It was him.
Bob is lovingly remembered by his wife of 66 years, Diana; his sons, Chris (Diane) and Wes; his grandchildren, Cassandra, Bennett, Ellie, and Dale; and his great-granddaughter, Casey. He will also be missed by many friends, teammates, fellow Legion members, and all who were fortunate enough to know him.
The family invites friends and relatives to join them for a celebration of Bob's life at the Erin Legion on Sunday, November 8, 2026, from 2:00 p.m. to 5:00 p.m.
In lieu of flowers, please send donations to the Legion.
A tree will be planted in memory of Brian in the Dods & McNair Memorial Forest at the Island Lake Conservation Area, Orangeville.
Condolences may be offered to the family at
Today, families looking for funeral homes in Caledon and Orangeville select Dods & McNair Funeral Home for a cremation or burial service.
