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100

A scammer creates a fake email and sends it to thousands of people, hoping some of them will click on a link and give up their personal information. 

What is Phishing?


100

This service allows users to remain anonymous, masking their identity/location and encrypts traffic.

Hint: You should be using this at Starbucks!

What is a VPN or Virtual Private Network?

100

Under Canadian breach rules, organizations must keep records of every breach for this period.

What is 24 months?

100

This Toronto franchise is often called the oldest professional football team in North America.


Who are the Toronto Argonauts?

100

This forward is listed as Canada men’s all-time leading scorer.


Who is Jonathan David?

100

This 1904 disaster destroyed much of Toronto’s downtown commercial district.


What is the Great Fire of Toronto?

200

An independent malware program that self-replicates in order to spread from machine to machine to cause damage.

What is a (computer) worm?

200

In Canada, this federal privacy law governs many private-sector breach-reporting obligations.

What is PIPEDA?

200

Toronto was incorporated as a city in this year.

What is 1834?

200

These two seasons gave the Blue Jays back-to-back World Series titles.


What are 1992 and 1993?

200

Canada’s first match of the 2026 World Cup ended in this score against Bosnia and Herzegovina.


What is 1–1?

200

This nickname, later popularized by Drake, refers to Toronto’s six former municipalities.


What is The 6ix?

300

This common email mistake happens when sensitive information is sent to the wrong recipient.

What is a misdirected email?

300

Proofpoint acquired this AI security company in February 2026.

What is Acuvity?

300

Proofpoint reporting cited millions of attacks using this scannable image format.

What are QR codes?  

300

This Raptors season ended with the franchise’s first NBA championship.


What is 2018–19?

300

This Toronto FC star became the club’s career goals leader.

Who is Sebastian Giovinco?

300

Toronto’s original town grid was near this modern downtown street.


What is Parliament Street?

400

This attack aims to make a service such as a website unusable by “flooding” it with malicious traffic or data from multiple sources (often botnets).

What is Distributed Denial of Service (DDoS)?

400

This is a method of access control by which users must present multiple, separate pieces of identification, such as a password and keycard, in order to access a system.

What is multi-factor authentication?

400

According to IBM’s 2025 Cost of a Data Breach reporting, this was the average global time to identify and contain a breach.

What is 241 days?

400

This Blue Jays slugger is the franchise’s all-time home run leader.


Who is Carlos Delgado?

400

This Canadian scored the country’s first men’s World Cup goal in 2022.


Who is Alphonso Davies?

400

This Toronto neighbourhood preserves many 19th-century industrial buildings tied to Gooderham and Worts.


What is the Distillery District?

500

Criminals access someone's computer and encrypt the user's personal files and data. The user is unable to access this data unless they pay the criminals to decrypt the files. 

500

When a URL has this at the beginning, it means that the information entered into the site is encrypted

500

Ingram Micro was founded in this year.

What is 1979 as Micro D, Inc.

500

This Maple Leafs player became the franchise’s all-time goals leader.

Who is Auston Matthews?

500

This midfielder is listed as Canada men’s most capped player.


Who is Atiba Hutchinson?

500

In 1998, Toronto merged with surrounding municipalities in this controversial process.


What is amalgamation?