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Simon Derrick, chief currency strategist at BNY Mellon, raised concerns Monday around recent market moves.
"Without wishing to be too alarmist, there have been a few parallels to what was happening 30 years ago in terms of what's been happening to the dollar, what's been happening to oil prices, what's been happening to Treasury yields," he told CNBC's "Squawk Box Europe."
"It's all very September/October 1987 from that perspective."
Derrick referred to the volatile market, dubbed "Black Monday," that began on October 19, 1987, in Asia before spreading to Europe and then the United States later in the day. The Dow Jones industrial average fell more than 500 points — or 22 percent — in a single day.
Last week, major markets fell deep into the red with fears of an escalating trade war between the U.S. and China. Higher Treasury yields — effectively the cost of borrowing in the U.S. — also unnerved investors, as well as political problems in Italy and worries over Brexit negotiations in the U.K.
Derrick was adamant that current events wouldn't play out like they did 1987, but said a "confluence of different circumstances" could lead to a serious risk-off event, leading the market to get significantly worse this week.
"Could it get significantly worse (this week)? Yes," he said.
One of those circumstances was a no-deal Brexit, Derrick explained, as negotiations between the U.K. and the EU continue to influence sterling's value and investor confidence.
The U.K. leaves the bloc on March 29, by which time an agreement will have to be negotiated with the EU and voted through by the country's parliament to avoid a no-deal Brexit. Parliament's vote, according to Derrick, is where sterling's value truly hangs in the balance.
"Ironically, from the perspective of those that were looking for the possibility of a second referendum, no deal coming back might be the best thing because the likelihood of that being voted through parliament is incredibly low," he said.
"So the reaction of sterling only coming off modestly — we're still in the 1.30s against the dollar — is probably the right thing, it's not at this point that you're going to see the reaction, it's whatever parliament decides ultimately that's going to be the determinant in this.
"The danger is that, in all of this, if we come back and there's no deal, that actually we end up in stasis, we end up in gridlock in parliament and actually the default is that we end up in the end of March with Article 50 being triggered with no deal, that's the worst case."
He speculated that as long as a second referendum on Brexit remained a possibility, the pound would stay relatively stable.
"In terms of positioning for sterling, what you're tending to see is a little bit of a pull back from the stress levels you had over the summer," he said. "People become a little more relaxed, maybe precisely because they do think there's a chance of a second referendum. I think maybe that's why we are a little calmer than perhaps you would have thought given the headlines."
Aside from Derrick's comments, many strategists remain confident that global markets will bounce back despite continued volatility.
Amanda Agati, PNC Financial's co-chief investment strategist, told CNBC's "Trading Nation" Friday that the she believed strong earnings in the third quarter would revitalize the markets.
"We really think that Q3 (the third quarter) is going to set up to be pretty solid," she said. "As long as Q4 guidance looks pretty solid too, I think that's great news for the market."
Meanwhile, Raymond James' Jeffrey Saut told CNBC on Monday he also believed earnings reports could spark a market turnaround.
"Earning season's coming up, I think that's going to be the catalyst for the equity markets to trade back up to all-time highs," he said.
—CNBC's Kellie Ell contributed to this article.