Harry Winston Diamond Corporation

ANNUAL GENERAL MEETING | JUNE 2010

Forward-Looking Information
Information in this disclosure that is not current or historical factual information may constitute forward-looking information or statements within the meaning of applicable securities laws. Forward-looking information is based on certain factors and assumptions regarding, among other things, mining, production, grade and tonnage, construction and exploration activities at the Diavik Diamond Mine, world and US economic conditions, the worldwide demand for luxury goods and the level of worldwide diamond production. Specifically, in making statements regarding expected diamond prices and expectations concerning the diamond industry and expected sales trends, margins, profitability and market conditions in the retail segment, Harry Winston Diamond Corporation (the Company) has made assumptions regarding, among other things, continuing recovery of world and US economic conditions, diamond supply and demand for luxury goods. Forward-looking information may relate to managements future outlook and anticipated events or results, and may include statements or information regarding plans, timelines and targets for construction, mining, development, production and exploration activities at the Diavik Diamond Mine, future mining activities and processing at the Diavik Diamond Mine, projected capital expenditure requirements and the funding thereof, liquidity and working capital requirements and sources, estimated reserves and resources at, and production from, the Diavik Diamond Mine, the number and timing of expected rough diamond sales, expected diamond prices and expectations concerning the diamond industry and the demand for luxury goods, expected cost of sales and gross margin trends in the mining segment, and expected sales trends and market conditions in the retail segment. Actual results may vary from the forward-looking information. While the Company considers these assumptions to be reasonable based on the information currently available to it, they may prove to be incorrect. Forward-looking information is subject to certain factors, including risks and uncertainties, which could cause actual results to differ materially from what we currently expect. These factors include, among other things, the uncertain nature of mining activities, including risks associated with underground construction and mining operations, risks associated with joint venture operations, risks associated with the remote location of and harsh climate at the Diavik Diamond Mine site, risks associated with regulatory requirements, fluctuations in diamond prices and changes in US and world economic conditions, the risk of fluctuations in the Canadian/US dollar exchange rate, cash flow and liquidity risks, risks relating to the Companys salon expansion strategy and competition in the luxury jewelry segment as well as changes in demand for high end luxury goods. Readers/viewers are cautioned not to place undue importance on forward-looking information, which speaks only as of the date of this disclosure, and should not rely upon this information as of any other date. While the Company may elect to, it is under no obligation and does not undertake to update or revise any forward-looking information, except as required by law. Additional information concerning factors that may cause actual results to materially differ from those in such forward-looking statements is contained in the Harry Winston Diamond Corporations filings with Canadian and United States securities regulatory authorities and can be found at www.sedar.com and www.sec.gov respectively.

Agenda Introduction Financial Highlights Retail Segment Mining Segment Q & A Session

Harry Winston: The Unique Proposition

The Diavik Mine

PICE INFOMATION

Diavik Mine Supply

SUPPLY LEVERAGE

Price?

Cutters/Polishers

Harry Winston: The Unique Proposition

The Diavik Mine

PICE INFOMATION

Diavik Mine Supply

SUPPLY LEVERAGE

Price?

Cutters/Polishers

Other Rough Diamond Suppliers

Other Jewelers

Harry Winston: The Unique Proposition

The Diavik Mine

PICE INFOMATION

Retail Customer

Diavik Mine Supply

PRICE INFORMATION SUPPLY

LEVERAGE

Harry Winston Retail Demand

Cutters/Polishers

Other Rough Diamond Suppliers

Other Jewelers

Harry Winston: The Unique Proposition

The Diavik Mine

PICE INFOMATION

Retail Customer

Diavik Mine Supply

PRICE INFORMATION SUPPLY

LEVERAGE SUPPLY LEVERAGE

Harry Winston Retail Demand

Cutters/Polishers

Other Rough Diamond Suppliers

Other Jewelers

Diamond Prices Have Recovered Rapidly

Indexed on S&P/Goldman Sachs spot metal prices and Harry Winston rough sales indexed to shipment 01/07

Rough Prices Underpinned by Polished

Harry Winston rough sales and polished purchases indexed to January 2008

Financial Highlights

10

Turnaround Began in Q4 FY2010

Consolidated Sales
Q1
186 156

Q2

Q3

Q4

149

+14%
134 118

-29%
110

-49%
95

-50%
75

FY 2009

FY 2010

FY 2009

FY 2010

FY 2009

FY 2010

FY 2009

FY 2010

(in millions of US dollars)

11

And Continued in Q1 FY2011

Consolidated

Sales
114

Gross Margin

EBITDA1

110

37 26 23 8

Q1 FY2010

Q1 FY2011

Q1 FY2010

Q1 FY2011

Q1 FY2010

Q1 FY2011

(in millions of US dollars)

1

EBITDA is earnings before interest, taxes, depreciation and amortization.

12

Mine Plan Contemplated Lower Production in Q1 FY2011

Mining Segment
Carats Recovered1
714

Sales

625

58 49

Q1 Q1 CY 2009 CY 2010 (in thousands) (in millions of US dollars except carat amounts)
1

Q1 FY 2010

Q1 FY 2011

Represents 40% share of Diavik Production

13

Underlying Strength in Rough Market

Mining Segment

Achieved Price
98%

EBITDA1

18 10

Q1 FY 2010
-54%

Q1 FY 2011

(in millions of US dollars) Q1 FY 2011

Q1 FY 2010

EBITDA is earnings before interest, taxes, depreciation and amortization.

14

Mining Segment Full Year Growth

Carats Recovered 1
3,690 328 +/-3,200

Sales

EBITDA 2

2,226

233 188

625 45

CY CY CY 2008 2009 2010 (in thousands) (in millions of US dollars except carats amounts)
1 2

FY 2009

FY 2010

FY 2011

FY 2009

FY 2010

FY 2011

Represents 40% share of the Diavik production EBITDA is earnings before interest, taxes, depreciation and amortization.

15

Retail Segment Shows Considerable Improvement in Q1 FY2011

Sales

Gross Margin

EBITDA1

65 52 25 5

34

-2

Q1 FY2010 (in millions of US dollars)

1

Q1 FY2011

Q1 FY2010

Q1 FY2011

Q1 FY2010

Q1 FY2011

EBITDA is earnings before interest, taxes, depreciation and amortization.

16

Expected to Continue for the Year

Retail
Sales
281

Gross Margin
133

EBITDA1

225

108

10

-3

FY 2009

FY 2010

FY 2011

FY 2009

FY 2010

FY 2011

FY 2009

FY 2010

FY 2011

(in millions of US dollars)

1

EBITDA is earnings before interest, taxes, depreciation and amortization.

17

Significant Balance Sheet De-leveraging

Consolidated
FYE 2009 January 31, 2009 FYE 2010 January 31, 2010 Q1 FY 2011 April 30, 2010
90 63 47

-108 -122 -185 -198 -276 -323

Debt

Cash

Net Debt

Debt

Cash

Net Debt

Debt

Cash

Net Debt

(in millions of US dollars)

18

Significant Balance Sheet De-leveraging

Mining Segment

FYE 2009 January 31, 2009

FYE 2010 January 31, 2010

Q1 FY 2011 April 30, 2010

62 41 -7 45 38 39

-23

-64 -105

Debt

Cash

Net Debt

Debt

Cash

Net Cash

Debt

Cash

Net Cash

(in millions of US dollars)

19

Significant Balance Sheet De-leveraging

Retail Segment
FYE 2009 January 31, 2009 FYE 2010 January 31, 2010 Q1 FY 2011 April 30, 2010

28 6 18

-160 -178 -218 -212

-148 -176

Debt

Cash

Net Debt

Debt

Cash

Net Debt

Debt

Cash

Net Debt

(in millions of US dollars)

20

Retail Segment
21

Retail Segment Our Mission

The Harry Winston Brand

Trends in the Global Luxury Market Five Year Growth Plan Financial Vision

22

Retail Segment Mission Statement

Create financial value for Shareholders, by creating emotional value for Clients and goodwill from Society,

by being the most exclusive Diamond Jeweler and Watchmaker in the world.

23

Retail Segment Financial Vision

FY2010 Last year Revenue Gross Margin % Operating Profit % EBITDA % $225M 48% -7% -1.2%

FY20131

FY20161

20% CAGR +/- 51% +/- 7% +/- 11%

15% CAGR +/- 52% +/- 12% +/- 15%

Figures for internal planning and measurement purposes. This is not a forecast of actual results.

24

Brand Mission Statement

Celebrate the meaningful moments of our clients lives

25

Retail Segment Our Mission

The Harry Winston Brand

Trends in the Global Luxury Market Five Year Growth Plan Financial Vision

26

Harry Winston is a Brand..

for Meaningful Moments

Luxury is about celebrating relationships & giving Emotion, gratitude, attachment, commitment, love

with Meaningful Products

Adamas. Diamonds are timeless symbols of power and purity.
Best Quality: capture the rarest essence of nature Best Craftsmanship: express the genius of man, shaping nature and time

by Meaningful People
Harry Winston people are: Knowledgeable, passionate, trustworthy, service oriented

27

Heritage is a Source of Power

Jennifer Jones, Hollywood, 1944

Harry Winston invents Red Carpet dressing

Lesotho, Jonker, Star of Sierra Leone

Mythical Gemstones owned by Harry Winston
28

Innovation is a Source of Power

Pioneer of modern jewelry craftsmanship

Invention of fluid shapes and the Cluster Design

The youngest legitimate Horology Brand

In one decade, Opus has gained the respect of centuryold brands
29

Philanthropy is a Source of Power

1958, Harry Winston donates Hope to the World

A chief act of generosity, 2nd most visited artifact in the world

Court of Jewels- the heart of American philanthropy

The first socially responsible jeweler was born
30

Retail Segment - Market Opportunity

A Jewelry market over $150 billion1, 85% of which is unbranded Brands bring a sense of History, Social Status & Style Guidelines Branding Phenomenon in the 2000s: Luxury and Fashion brands are set to conquer the jewelry field

Market Shift to Branded Jewelry

Sources: Company estimates based on multiple sources

Page 31

Retail Segment Our Mission

The Harry Winston Brand

Trends in the Global Luxury Market Five Year Growth Plan Financial Vision

32

Luxury in 2010 Entering a Post-recession Era Year 2010 growth forecast Global luxury market 5-10%
ASIA (ex-Japan) - Booming China 15%, Rest of Asia 10% THE WEST - Slow Recovery North America 4%, Europe 3% JAPAN - Still very Profitable but saturated Japan -3%

Sources: Bain & Co, April 2010; American Express, 2010

33

Old World, Young World

The Global Age Gap Shaping Luxury Markets

Source: CIA World Factbook, 2009

34

Where the Wealthy Live

High Net Worth Individual Population by Region

Europe: 2.6M
2005-2008: +7.7%

North America: 2.7M

2005-2008: -7.4%

Asia Pacific Middle East: 0.4M (incl. Japan): 2.4M

2005-2008: +25% 2005-2008: 0%

Africa: 0.1M
2005-2008: 0%

Latin America: 0.4M

2005-2008: +25%

Sources: CapGemini Merrill Lynch, 2009 Footnote: HNWI: People with more than 1 million dollars in investable assets excluding primary residence, collectibles, consumables and consumer durables

35
Page 35

At the Very Top

Top countries and cities with billionaires

In 2010,China has the most billionaires outside of the US Closely followed by Russia, Germany and India HW already has a strong presence in key cities where top billionaires reside

City New York Moscow London Istanbul Los Angeles Hong Kong Mumbai Dallas San Francisco Tokyo

Number of billionaires 60 50 32 28 27 25 20 17 14 14

Harry Winston Retail Presence

Source: Forbes, 2010

36

Luxury Consumers and the Internet

Luxury consumers declare the Internet is the most useful source of information for them 80% of wealthy consumers use search engines on a daily basis Luxury consumers shop both online and in stores On average, Internet users are richer and younger than instore shoppers

Sources: Google, 2008; Luxury Institute, 2010

37

Retail Segment Our Mission

The Harry Winston Brand

Trends in the Global Luxury Market Five Year Growth Plan Financial Vision

38

Retail Segment - Strategic Statement

Create a Global and Scalable platform,

to substantially Grow Sales and Profitability over five years,

through an Integrated Marketing strategy

39

Branding Strategy Consolidate & Expand our Position

Exclusivity Scale Expressed through: Price points Number of Stores Consumer Perception

Bespoke

Ultra High-End

Core & Premium Luxury

Generalist watch & jewelry brands Designer accessories & apparel

Affordable / Everyday Luxury

Designer Eyewear, Fragrances, Spirits, Silver Jewelry

Target Consumer Base Size

40

Branding Blend Tradition & Innovation

Rejuvenate the delivery of our message to appeal to the new generation Use our name & history to boost our communication exposure Harry Winston: a Brand of extremes, uncompromising

41

Jewelry Collections Strengthen the Iconic High End

Reinforce our core product segment Revive our legacy business, use the umbrella effect

Become a Bridal Destination

Use our legitimacy in diamonds to gain market share in a highly competitive market

Collections: Modern, Creative, Innovative

Rejuvenate our offer, appeal to a younger clientele

42

Timepieces Collections

Rationalize, broaden our offer

More compact collections for more commercial impact & better product rotation Introduce variety in designs to target different market segments

Optimize Margins & Assortment

Use our scalable manufacturing capacity to improve gross margins

43

Communication Amplify, Integrate, Synchronize

Public Relations Advertising

Website / Online Marketing

Printed Material

Exhibition Design

Harry Winstons Message

Visual Merchandising

Packaging

Media Planning
44

Retail Salon Network

Salon Profitability Action Plans

Focused action plans to improve existing Salon profitability

Capture Growth Opportunities

Asia (ex-Japan)
Japan Europe

45

Retail Network Today

North America 8 Salons

Europe 2 Salons Asia

(ex-Japan)

Japan 5 Salons

4 Salons

46

Projected Retail Network by 2016

Europe 6 Salons North America 9 Salons Asia (Ex-Japan) 13 Salons

Japan 7 Salons

47

Other Channels

Wholesale
Room for growth: develop network of authorized watch retailers

Partner Salons: Hybrid Distribution Model

Harry Winston Salons operated by business partners Maintain control of Brand image Limit company exposure in riskier markets

Exhibitions & E-commerce

Extend our reach while minimizing operating costs

48

Retail Segment Our Mission

The Harry Winston Brand

Trends in the Global Luxury Market Five Year Growth Plan Financial Vision

49

Retail Segment Financial Vision

FY2010 Last year Revenue Gross Margin % Operating Profit % EBITDA % Operated Salons Partner Salons Wholesale Doors
1

FY20131

FY20161

$225M 48% -7% -1.2% 19 0 188

20% CAGR +/- 51% +/- 7% +/- 11% +/- 26 +/- 12 250+

15% CAGR +/- 52% +/- 12% +/- 15% +/- 35 +/- 20 300+

Figures for internal planning and measurement purposes. This is not a forecast of actual results.

50

Mining Segment
51

Diavik Mine: Reserves and Resources

A21
9400 L 9350 L 9300 L Measured Resource 9250 L 9200 L Indicated Resource Inferred Resource Exploratory 9150 L 9100 L 9050 L 9000 L 8950 L 8900 L 8850 L

8800 L
8750 L 8700 L

52

Exceptional grade makes Diavik one of the highest value tonne mines
Rock Value US$/Tonne for Major Kimberlites
Relative to 2008 Production Value
$350

Snap Lake $148m Victor $299m

$300 $250

Venetia $638m

Ellendale $109m Finsch $197m Argyle $211m Letseng $215m

$150 $100 $50 $0

$8,000m

Catoca $451m

Orapa $1,000m

$7,000m

$6,000m

Udachny $796m

Aikhal $372m

$200

Letlhakane $240m

$5,000m

Nyurba $596m

$4,000m

$3,000m

$2,000m

Ekati $535m

Rock Value per tonne in millions of US dollars

Jwaneng $1,709m

$1,000m

Diavik $800m
$0m

Production value in millions of US dollars

Source: Based on 2008 data from Company Estimates, Annual Reports, BMO Diamond Research (Jan 2009)

Mir $546m

53

World Diamond Production

Gem diamond production (value) Total US$14.8 billion
Other (highly fragmented) 27%

De Beers 40%

Alrosa 19% Harry Winston Rio Tinto BHP 4% 6% 4%

Other (fragmented) includes: Artisanal & Illicit (8%) and Juniors (19%) Source: De Beers estimates 2008

54

Underground Mining Methods

55

Underground Mining Methods

56

Underground Mining Methods

Sublevel Caving

57

Diamonds are Different

100% 1% 29% 80% 6%

12% 60% 99% 40% 73%

58%
20% 23%

0%

Diamonds

Gold

Platinum

Jewellery

Industrial and Autocatalyst

Investment

Source: De Beers Group analysis; World Gold Council Gold Demand Trends, February 2009; Angloplat 2008 Annual Report, page 20

58

Diamond Exploration Challenge

Diamond exploration results from the last 140 years

5,000 5,000

1,500

1,025 1,000 850

500

50 0

Kimberlites sampled

Diamondiferous

Economic

Gold Mines

Source: De Beers exploration data (diamonds) and Metals Economic Group (gold mines)

59

Diavik Exploration Potential

60

World Supply Reducing

No new material production is expected to come online in the near future

Source: De Beers

61

Diavik Underground is a Major Development Project

Rock Value US$/Tonne for Advanced Projects
Relative to 2008 InSitu Value Estimates

Rock value per tonne in millions of US dollars

Value estimates in millions of US dollars

Source: Based on Janse/Read: Diamonds (15 March 2009), Company Estimates, Public Company data

62

Diavik and Harry Winston

premium assets supporting each other

63