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Grant of Options to Director and Employees

29 November 2019 – London, UK Crossword Cybersecurity Plc (AIM:CCS, “Crossword”, the “Company” or the “Group”), the technology commercialisation company focused solely on cyber security and risk, is pleased to announce that it has granted 7,958 options comprising 2,250 options under the Company’s Enterprise Management Incentive Scheme (the “EMI Plan”) and 5,708 options under the Non Tax Advantaged Plan. The 7,958 options granted vest in three equal tranches on first, second and third anniversary of the date of grant and are exercisable into 7,958 ordinary shares of £0.05 each in the Company (“Ordinary Shares”) at a price of £4.80 per share.

Included in the above number are options to a Director as set out below:

Sir Richard Dearlove

The Company today has granted to Sir Richard Dearlove an option pursuant to the rules of the Non Tax Advantaged Plan to acquire 5,208 Ordinary Shares at an exercise price of £4.80 per share.

Following this grant, Sir Richard Dearlove holds options over 29,710 Ordinary Shares in the Company.

Following this grant of options, the total number of options outstanding under the EMI Plan will be 77,179. A further 113,210 options are outstanding under an unapproved share scheme. The total number of options outstanding following this grant will be 190,389 representing 4.07% of Crossword’s issued share capital.

The following notifications, made in accordance with the requirements of the EU Market Abuse Regulation, gives further details.

1

Details of the person discharging managerial responsibilities / person closely associateda)NameSir Richard Dearlove

2

Reason for the notificationa)Position/statusChairmanb)Initial notification /AmendmentInitial Notification

3

Details of the issuer, emission allowance market participant, auction platform, auctioneer or auction monitora)NameCrossword Cybersecurity plcb)LEI213800FJNJGZBUSOZQ63

4

Details of the transaction(s): section to be repeated for (i) each type of instrument; (ii) each type of transaction; (iii) each date; and (iv) each place where transactions have been conducteda)Description of the financial instrument, type of instrumentIdentification codeOptions to acquire ordinary shares of 5p each at the price of £4.80 each For Ordinary Shares: GB00BPFJXS57b)Nature of the transactionGranting of optionsc)Price(s) and volume(s)Price        Nil                Volume 5,208d)Aggregated informationPrice        Nil                 Volume 5,208e)Date of the transaction28/11/2019f)Place of the transactionOff-market transaction

Contacts

Crossword Cybersecurity plc – Tel: +44 (0) 20 3953 8460

Email: info@crosswordcybersecurity.com

Tom Ilube, Chief Executive Officer

Mary Dowd, Finance Director

Grant Thornton (Nominated Adviser) – Tel: +44 (0) 20 7383 5100

Colin Aaronson / Jamie Barklem / Niall McDonald

Hybridan LLP (Broker) – Tel: +44 (0)203 764 2341

Claire Louise Noyce

For media enquiries contact:

Lorena Duke, GingerPR

lorena@gingerpr.co.uk, 01932 485 300

About Crossword Cybersecurity plc

Crossword Cybersecurity plc focuses on the development and commercialisation of university research-based cyber security related software and cyber security consulting.  The Group’s specialist cyber security product development and software engineering teams work with its university partners to develop the research concept into a fully-fledged commercial product that it will then take to market. The Group’s aim is to build up a portfolio of revenue generating, intellectual property based, cyber security products. Rizikon Assurance, Crossword’s leading product, is a SaaS platform that enables medium to large companies to assess the cyber maturity and GDPR readiness of their suppliers. Nixer CyberML, Crossword’s most recently launched product, is a new tool for businesses that want to solve advanced security and cybercrime problems, such as detecting and dealing with compromised accounts, fraud and in-application denial of service attacks.  Crossword’s team of expert cyber security consultants leverages years of experience in national security, defence and commercial cyber intelligence and operations to provide bespoke advice tailored to its clients’ business needs.

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