Canadian Pacific Kansas City : CPKC 2024 Management Proxy Circular

2024 MANAGEMENT PROXY CIRCULAR TABLE OF CONTENTS

About the information in this proxy circular

Note regarding presentation

Our shares are listed for trading on the Toronto Stock Exchange (TSX) and the New York Stock Exchange (NYSE). We are classified as a foreign private issuer pursuant to applicable U.S. securities laws and are therefore exempt from the proxy rules under the U.S. Securities Exchange Act of 1934, as amended (Exchange Act). This document is prepared in compliance with applicable Canadian securities laws and regulations. Additionally, as a foreign private issuer, we are permitted to follow home country practice instead of certain governance requirements set out in the NYSE rules, provided that we disclose any significant differences between our governance practices and those required by NYSE rules on our website at investor.cpkcr.com/governance.

Non-GAAP measures

This proxy circular includes certain measures that do not have standardized meaning and are not defined by generally accepted accounting principles (GAAP) in the United States and, therefore, may not be comparable to similar measures used by other companies. These non-GAAP measures include core adjusted combined operating income, core adjusted combined operating ratio, core adjusted combined diluted earnings per share (EPS), core adjusted combined return on invested capital (ROIC), adjusted combined free cash, and adjusted combined net debt to adjusted combined earnings before interest, tax, depreciation and amortization (EBITDA) included in the compensation discussion and analysis beginning on page 32. You can find more information about non-GAAP measures and the definitions of these measures on page 105.

Forward-looking information

This proxy circular contains certain forward-looking information and forward-looking statements (collectively, "forward- looking information") within the meaning of applicable securities laws relating to our compensation programs, operations, anticipated financial performance, business prospects, planned capital expenditures and strategies, and board and committee composition and roles, among other things. Any statements about our expectations, beliefs, plans, goals, targets, predictions, forecasts, objectives, assumptions, information and statements about possible future events, conditions and results of operations or performance are not historical facts and may be forward-looking.Forward-looking information in this proxy includes, but is not limited to, plans or objectives of management for future operations; information regarding sustainability- related actions we plan to take in the future, including our Climate Strategy and our goals and commitments for reducing greenhouse gas (GHG) emissions. Forward-looking information is often, but not always, made through the use of words or phrases such as "anticipates", "aims", "believes", "can", "could", "may", "predicts", "potential", "should", "will", "estimates", "plans", "targets", "projects", "continuing", "ongoing", "expects", "intends" and similar words or phrases suggesting future outcomes.

Forward-looking information is based on current assumptions about our business and our strategy as well as economic, political, regulatory, market and environmental conditions affecting them. Although we believe the assumptions reflected in the forward-looking information presented in this proxy circular are reasonable as of the date hereof, there can be no assurance that they may prove to be correct. You should not put undue reliance on forward-looking information, as it is not a guarantee of future performance. Forward-looking information involves many inherent risks and uncertainties that could cause actual results to differ materially from the forward-looking information. This includes risks such as: changes in business strategies, general North American and global economic, credit and business conditions, changes in the availability and price of commodities and energy; the effects of competition; industry capacity; shifts in demand; changes in laws and regulations; natural or other disasters, including severe weather, earthquakes, wildfires, pandemics or acts of terrorism affecting the markets in which we operate; geopolitical uncertainty; the adverse effects of climate change on our business, investors, customers, suppliers and counterparts; cybersecurity attacks, as well as security threats and governmental response to them; our ability to successfully execute on initiatives relating to sustainability; the quality and accuracy of information provided to us by third parties; cost increases; claims and litigation; labour disputes; liabilities arising from derailments and the pandemic created by the outbreak of the novel strain of coronavirus (and the disease known as COVID-19) and its variants; satisfaction of the conditions imposed by the U.S. Surface Transportation Board (STB) in its March 15, 2023 decision and successful integration of Kansas City Southern (KCS) into the Company, among other things. The foregoing list of risks is not exhaustive.

2 CPKC

These and other factors are detailed from time to time in reports we file with the securities regulators in Canada and with the U.S. Securities and Exchange Commission (SEC) in the United States. You should refer to Item 1A - Risk Factors and Item 7 - Management's Discussion and Analysis of Financial Condition and Results of Operations and Forward-LookingInformation in our 2023 annual report on Form 10-K and to our risk factor and forward-looking information disclosure in our annual and interim reports filed on SEDAR+ (www.sedarplus.ca) and EDGAR (www.sec.gov).

Forward-looking information is based on our current expectations, estimates and projections, and it is possible we will not achieve these predictions, forecasts, projections and other forms of forward-looking information. Unless indicated otherwise or the context otherwise requires, this proxy circular speaks only as of the date hereof. We undertake no obligation to update or otherwise revise any forward-looking information, unless we are required to by applicable law.

In addition, there can be no guarantee that our strategy for, or targets and commitments related to, reducing GHG emissions will be achieved. Our Climate Strategy (including our strategy, commitments and targets for reducing GHG emissions) continues to evolve as we continue to refine our analysis of and response to potential future climate risks and opportunities, and as the science, data, standards, regulations and methodology underlying our analysis and strategy continue to change over time.

Therefore, in future disclosures, we may present information (including both forward-looking and historical information) that differs from the information contained in this proxy circular. We undertake no obligation to update or otherwise revise such information, unless we are required by applicable law.

Explanatory notes

Kansas City Southern transaction

On December 14, 2021, the Company completed its acquisition of KCS pursuant to an Agreement and Plan of Merger (Merger Agreement) with KCS. On April 14, 2023 (the Control Date), following final approval granted by the U.S. Surface Transportation Board on March 15, 2023 (STB March 15 Decision), CP obtained control of KCS.

For more information regarding the KCS acquisition, see our Annual Report on Form 10-K for the fiscal year ended December 31, 2023 and our Notice of Special Meeting and Management Proxy Circular dated November 1, 2021 in respect of the special meeting of shareholders held on December 8, 2021 in connection with the KCS acquisition (Special Meeting). For more information regarding the STB March 15 Decision and the completion of the transactions contemplated under the Merger Agreement, see our Current Reports on Form 8-K filed with the SEC on EDGAR (www.sec.gov) and filed on SEDAR+ (www.sedarplus.ca) on March 16, 2023, March 17, 2023 and April 14, 2023 and our Material Change Reports filed on SEDAR+ on March 16, 2023, March 20, 2023 and April 14, 2023.

Unless indicated otherwise or the context otherwise requires, in this proxy circular, references to Canadian Pacific Kansas City Limited, CPKC, the Company, or the Corporation, "we", "us" or "our" with respect to or including a time period prior to April 14, 2023 (being the Control Date) refer to or include the Company as it existed prior to (i) completion of the acquisition of control of KCS and (ii) its name change from "Canadian Pacific Railway Limited" to "Canadian Pacific Kansas City Limited". Any references herein to "on a standalone basis" or other references to "standalone" refer to the Company either prior to the acquisition of control of KCS, or otherwise excluding KCS.

Share Split

On April 21, 2021, the Company's shareholders approved a five-for-one share split of the Company's issued and outstanding shares (the share split). On May 13, 2021, the Company's shareholders of record as of May 5, 2021 received four additional shares for every share held. Ex-distribution trading in the shares on a split-adjusted basis commenced on May 14, 2021. Proportional adjustments were also made to outstanding awards under the Company's stock-based compensation plans in order to reflect the share split. All shares and notional units have been adjusted to reflect the share split, unless noted otherwise.

2024 MANAGEMENT PROXY CIRCULAR 3

In this document, unless indicated otherwise or the context otherwise requires:

• "Board" means the Board of Directors of CPKC
• "Control Date" means April 14, 2023, the date on which CPKC (through an indirect wholly owned subsidiary) assumed control of KCS's railroad operations pursuant to the final, non-appealable March 15, 2023 approval by the U.S. Surface Transportation Board of such control
• "CP" means the Company either prior to the acquisition of control of KCS, or otherwise excluding KCS, as described in "Explanatory notes" starting on page 3
• "KCS" means Kansas City Southern
• "KCS transaction" and "KCS acquisition" each mean the transactions contemplated under the Merger Agreement
• "Merger Agreement" means the Agreement and Plan of Merger dated September 25, 2021 between CPKC and KCS pursuant to which CPKC agreed to acquire KCS in a stock and cash transaction
• "shares" means common shares of CPKC
• "shareholders" means holders of our shares
• "you" and "your" refer to shareholders of Canadian Pacific Kansas City Limited
• "we", "us", "our", "CPKC", "Company" and "Corporation" refer to Canadian Pacific Kansas City Limited (known as Canadian Pacific Railway Limited until April 14, 2023 or the Control Date) and, where applicable, its subsidiaries (which excludes KCS with respect to the period prior to April 14, 2023)
• all amounts are in Canadian dollars
• any 2023 amounts paid in United States dollars (US$) have been converted to Canadian dollars using the Bank of Canada average exchange rate for the year ended December 31, 2023 ($1.3497 = US$1.00) unless otherwise stated
• information in this document is as of March 12, 2024 unless otherwise indicated

For more information

You can find more information about CPKC, including our 2023 annual report, on our website (investor.cpkcr.com), on SEDAR+ (www.sedarplus.ca) and on EDGAR (www.sec.gov). You can also ask us for a free copy of the annual report by writing to:

Office of the Corporate Secretary

Canadian Pacific Kansas City Limited

7550 Ogden Dale Road S.E.

Calgary, Alberta T2C 4X9

4 CPKC

ABOUT CPKC

Founded in 1881 to connect Canada, today we deliver transportation solutions across the only rail network connecting North America including Canada, the United States and Mexico. We create long-term sustainable value for our shareholders and the broader economy by delivering safely and efficiently for our customers. We leverage our precision scheduled railroading foundations: provide service; control costs; optimize assets; operate safely; and develop people in all that we do. CPKC's culture is guided by three core values: accountability, diversity and pride. These values drive our actions, foster respect and inspire our journey towards excellence.

Our proud railroaders are building on the legacy of the people who envisioned and built our historic railroad. Throughout its history, our railroaders have defied those who said it couldn't be done. The accountability and drive to deliver results is ingrained in our culture. The people who power our railroad are determined to redefine expectations of a Class I railroad today, while always keeping an eye on greater things ahead.

At CPKC, we are serving today and building for the future.

Our network - connecting a continent

2024 MANAGEMENT PROXY CIRCULAR 5

MESSAGE FROM THE CHAIR OF THE BOARD

Fellow Shareholders,

On behalf of the Board of Directors, I am pleased to invite you to the shareholder meeting for Canadian Pacific Kansas City Limited (CPKC). CPKC's 2024 annual meeting of shareholders will take place online on April 24, 2024 at 9 a.m. (Mountain Daylight Time) and will be streamed via live webcast over the internet at: https://web.lumiagm.com/ 452600803. As in past years, shareholders will be able to vote as they would in an in-person shareholder meeting. Shareholders who usually vote by proxy ahead of the meeting will be able to do so in the usual way. More details about voting can be found at page 98 of this proxy circular.

Items at the meeting

At the meeting, you will vote on several items of business, including the election of directors, the "say on pay" non-binding advisory vote on executive compensation, approval of our auditor and a non-binding advisory vote on our approach to climate change. This is our third year of asking for shareholders to vote on our approach to climate change.

A transformative year

I want to congratulate our President and CEO Keith Creel and the entire CPKC family of railroaders for delivering a transformative year. Final STB approval of our merger with Kansas City Southern was received on March 15, 2023 with the two companies combining as of April 14, 2023. I was in Kansas City on this historic day where we held a special celebration and drove a ceremonial "Final Spike" to celebrate this momentous merger. The Board has supported management with the transaction in numerous ways. We have established an Integration Committee, led by former President of the Association of American Railroads, the Hon. Ed Hamberger. The Integration Committee has focused on monitoring compliance with STB conditions, monitoring achievement of revenue and expense synergies and will continue to monitor our integration planning and offer guidance on issues that may arise. Ed and the Board have worked closely with management to measure synergies so CPKC can realize the benefits of the transaction. The Integration Committee will also work directly with the Board to monitor our customer service, our new service offerings including the Mexico Midwest Express train from Mexico to Chicago, Illinois and our overall operating performance.

Since April, our Board has been active across the vast new network and has held meetings in all three countries. In advance of the merger, we developed a comprehensive board integration plan which we executed throughout 2023. At our April Board meetings, we toured part of our legacy network between Calgary and Banff. The Board attended a meeting of our Mexico subsidiary, Kansas City Southern de México, S.A. de C.V. in Mexico City in August. We attended a Mexico employee town hall at that time and met with key management and staff in Mexico. In September, the Board met in Kansas City for our strategy meetings. Among other things, we discussed the transformative power of artificial intelligence and its impact on all industries, including rail. Our greatest opportunity is to leverage the strengths of the combined franchise with legacy CP directors learning about the legacy KCS operations and legacy KCS directors learning about legacy CP operations.

I am proud to report that CPKC was named to the S&P Global Dow Jones Sustainability World Index (DJSI World) and North American Index (DJSI North America) in 2023. Our approach to climate change has been meaningfully influenced by the discussions we have had with shareholders over the last number of years. The ongoing "say on climate" vote continues to act as a mechanism for shareholders to provide their feedback and prompt further dialogue on this important topic. Importantly, in 2023 we continued to operate as one of the safest railroads in North America and we continued to leverage the strength of our Home Safe program which has been instrumental in lowering the number of workplace injuries.

This was the 25th year of our CPKC holiday train which raised a record $1.8 million dollars for foodbanks across North America. For the first time, our CPKC holiday train went south of Kansas City and included new destinations including Pittsburg, Kansas; Joplin, Missouri; Heavener, Oklahoma; Mena, Arkansas; Texarkana, Texas; and Shreveport, Louisiana.

6 CPKC

We also continued the legacy KCS tradition of the Holiday Express visiting 20 communities and raising more than US$200,000. Our Mexican train Tren Navideño also went to communities across Mexico. We will continue to work with management to integrate our combined North American CPKC culture.

Shareholder engagement

As we have done in past years, we continue to engage with our shareholders. This year, I have been accompanied by both Gordon Trafton (Chair of the Risk and Sustainability Committee) and the Hon. Ed Hamberger (Chair of the Integration Committee). We have been particularly focused on the Board's oversight of integration, our ongoing efforts to ensuring excellence in operating safety, our commitment to delivering synergies, our continued progress towards our climate goals, and the opportunities arising from technology and artificial intelligence. Our discussions, as they have in the past, will also focus on diversity, corporate culture and the ongoing integration, including employee retention. More information on our shareholder engagement strategy is at page 16 of this proxy circular.

Retention and Succession Planning

This year, the Board will be returning to eleven members, with ten independent directors. Jill Denham and David Garza-Santos will not be standing for election at the 2024 Annual Meeting. I want to thank Jill Denham for her remarkable eight year service on the Canadian Pacific and now CPKC Board. I also want to thank David Garza-Santos for his dedicated service to Kansas City Southern and his continued service this past year with CPKC. Being a railway that serves the populations in three countries, we are working to ensure that we are able to add another Mexico based director as soon as possible.

I thank you for your ongoing commitment to CPKC and look forward to your participation at our virtual shareholder meeting on April 24, 2024. In this proxy circular, you will find important information and instructions about how to participate at the virtual meeting. Please remember to vote your shares by proxy or online during the meeting. If you have any questions or require assistance voting, you can contact our strategic shareholder advisor, Kingsdale Advisors at 1-866-879-7649 (toll free in North America) or at 647-251-9709 (for collect calls outside of North America and for banks and brokers) in English, French or Spanish or by email at contactus@kingsdaleadvisors.com.

Sincerely,

Isabelle Courville

Board Chair

2024 MANAGEMENT PROXY CIRCULAR 7

PROXY HIGHLIGHTS

You have received this management proxy circular (proxy circular) because you owned shares of CPKC at the close of business on March 12, 2024 and are therefore entitled to participate in our 2024 annual meeting of shareholders and vote your shares.

The 2024 annual meeting will be held in a virtual format which will be conducted via live webcast online, allowing shareholders to participate regardless of where they are located. Shareholders will be able to vote on all business brought forth before the meeting and submit questions for consideration as they would at an in-person shareholders meeting. Questions that are not answered at the 2024 annual meeting will be addressed via email following the meeting. Shareholders that usually vote by proxy ahead of the meeting will be able to do so in the usual way.

Registered shareholders and duly appointed proxyholders will be able to participate in the meeting, participate in the question-and-answer session, and vote, all in real time, provided they follow the instructions in our proxy circular. Non-registered (or beneficial) shareholders that have not appointed themselves or another person as their proxyholder may attend the meeting online as guests.

In our continuing effort to reduce environmental impacts and improve sustainability, we have once again adopted the "notice and access" procedures permitted under applicable Canadian securities laws. Under the notice and access procedures, we can post electronic versions of the proxy circular and meeting materials online. Instructions for accessing these materials online will be mailed to shareholders in a notice. Shareholders can still obtain paper copies of the proxy circular and meeting materials upon request. For additional information, see Part VI - Delivery of Meeting Materials and Voting Information beginning on page 98.

Management is soliciting your proxy for the meeting, to be held virtually via live webcast as outlined below.

We are soliciting proxies by mail, in person, by phone or by electronic communications. The Corporation has retained Kingsdale Advisors to provide a broad array of strategic advisory, governance, strategic communications, digital and investor campaign services on a global retainer basis in addition to certain fees accrued during the life of the engagement upon the discretion and direction of the Corporation. Shareholders may contact Kingsdale Advisors, the Corporation's strategic advisor by telephone at 1-866-879-7649 or 1-647-251-9709 (text and call enabled outside North America), or by email at contactus@kingsdaleadvisors.com.

8 CPKC