Issue of Options to Employees and Directors

5 June 2019

Crossword Cybersecurity plc

(“Crossword ” or the ”Company”)

Issue of Options to Employees and Directors

Crossword Cybersecurity plc (AIM: CCS, “Crossword”, the “Company” or the “Group”), the cyber security technology commercialisation company, is pleased to announce that it has granted 42,354 options comprising 29,000 options under the Company’s Enterprise Management Incentive Scheme (the “EMI Plan”) and 13,354 options under the Non Tax Advantaged Plan.

Included in the above number are options to Directors 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 4,587 ordinary shares of £0.05 each in the Company (“Ordinary Shares”) at an exercise price of £5.45 per share.
Following this grant, Sir Richard Dearlove holds options over 24,502 Ordinary Shares in the Company.

Mary Dowd
The Company today has granted to Mary Dowd an option pursuant to the rules of the EMI Plan to acquire 10,000 Ordinary Shares at an exercise price of £5.45 per share.
Following this grant, Mary Dowd holds options over 17,936 Ordinary Shares.

Included in the 29,000 options granted under the EMI plan are the following options granted to members of the Company’s senior management.

Jake Holloway
The Company today has granted to Jake Holloway an option pursuant to the rules of the EMI Plan to acquire 5,000 Ordinary Shares at an exercise price of £5.45 per share.
Following this grant, Jake Holloway remains directly interested in 1,852 Ordinary Shares representing 0.04% of the Company’s total voting rights and options over 12,993 Ordinary Shares.

Stuart Jubb
The Company today has granted to Stuart Jubb an option pursuant to the rules of the EMI Plan to acquire 5,000 Ordinary Shares at an exercise price of £5.45 per share.
Following this grant, Stuart Jubb remains directly interested in 17,379 Ordinary Shares representing 0.37% of the Company’s total voting rights and options over 10,000 Ordinary Shares.

Of the 42,354 options granted, 36,837 Options, which were granted on 4 June 2019, vest in three equal tranches on first, second and third anniversary of the date of grant and are exercisable into 36,837 Ordinary Shares at a price of £5.45 per share and, 5,517 Options, which were granted on 16 January 2019 and vest in three equal tranches, on first, second and third anniversary of the date of grant and are exercisable into 5,517 Ordinary Shares at a price of £2.90 per share.

Following this grant of options, the total number of Options outstanding under the EMI Plan will be 76,429. A further 114,769 Options are outstanding under an unapproved share scheme. The total number of Options outstanding following this grant will be 191,198 representing 4.08% 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 associated
a) Name Sir Richard Dearlove

2. Reason for the notification
a) Position/status Chairmanb) Initial notification /Amendment Initial Notification

3. Details of the issuer, emission allowance market participant, auction platform, auctioneer or auction monitor
a) Name Crossword Cybersecurity plc
b) LEI 213800FJNJGZBUSOZQ63

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 conducted
a) Description of the financial instrument, type of instrument
Identification code Options to acquire ordinary shares of 5p each

For Ordinary Shares: GB00BPFJXS57
b) Nature of the transaction Granting of options
c) Price(s) and volume(s) Price £5.45 Volume 4,587
d) Aggregated information Price £5.45 Volume 4,587
e) Date of the transaction 03/06/2019
f) Place of the transaction Off-market transaction

1. Details of the person discharging managerial responsibilities / person closely associated
a) Name Mary Dowd

2. Reason for the notification
a) Position/status Finance Director

b) Initial notification /Amendment Initial Notification

3. Details of the issuer, emission allowance market participant, auction platform, auctioneer or auction monitor
a) Name Crossword Cybersecurity plc
b) LEI 213800FJNJGZBUSOZQ63

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 conducted
a) Description of the financial instrument, type of instrument
Identification code Options to acquire ordinary shares of 5p each

For Ordinary Shares: GB00BPFJXS57
b) Nature of the transaction Granting of options
c) Price(s) and volume(s) Price £5.45 Volume 10,000
d) Aggregated information Price £5.45 Volume 10,000
e) Date of the transaction 03/06/2019
f) Place of the transaction Off-market transaction

1. Details of the person discharging managerial responsibilities / person closely associated
a) Name Jake Holloway

2. Reason for the notification
a) Position/status Business Development Director

b) Initial notification /Amendment Initial Notification

3. Details of the issuer, emission allowance market participant, auction platform, auctioneer or auction monitor
a) Name Crossword Cybersecurity plc
b) LEI 213800FJNJGZBUSOZQ63

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 conducted
a) Description of the financial instrument, type of instrument
Identification code Options to acquire ordinary shares of 5p each

For Ordinary Shares: GB00BPFJXS57
b) Nature of the transaction Granting of options
c) Price(s) and volume(s) Price £5.45 Volume 5,000
d) Aggregated information Price £5.45 Volume 5,000
e) Date of the transaction 03/06/2019
f) Place of the transaction Off-market transaction

1. Details of the person discharging managerial responsibilities / person closely associated
a) Name Stuart Jubb

2. Reason for the notification
a) Position/status Managing Director – Consulting

b) Initial notification /Amendment Initial Notification

3. Details of the issuer, emission allowance market participant, auction platform, auctioneer or auction monitor
a) Name Crossword Cybersecurity plc
b) LEI 213800FJNJGZBUSOZQ63

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 conducted
a) Description of the financial instrument, type of instrument
Identification code Options to acquire Ordinary shares of 5p each

For Ordinary Shares: GB00BPFJXS57
b) Nature of the transaction Granting of options
c) Price(s) and volume(s) Price £5.45 Volume 5,000
d) Aggregated information Price £5.45 Volume 5,000
e) Date of the transaction 03/06/2019
f) Place of the transaction Off-market transaction

– Ends –

The information contained within this announcement is deemed to constitute inside information as stipulated under the Market Abuse Regulations (EU) No. 596/2014. Upon the publication of this announcement, this inside information is now considered to be in the public domain.

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

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. 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.