Was “matchmaking” the equivalent of today's “shipping”?
Solution 1:
Explaining the Difference
I strongly suspect that the reason an old word was effectively recycled is because the new word filled a lexical gap. It would not really make much sense to use matchmaking and shipping to mean the same thing.
A matchmaker would be somebody who exercises some influence over bringing two people together into an amorous relationship. The active role of a matchmaker bringing characters together makes it practically impossible to be one unless you exist within the same reality or fantasy as people to be matched. The exception is if you analogize the author to a deity, and writes the story as if a match was made in heaven (or heck, depending on the details of the story).
'Shipping, as I understand it as a long standing observer of a few video game and anime fandoms, it is moreso a term of a term of literary analysis used to describe an interpretation of a story that favors certain amorous pairings. It is a largely passive observation regarding interpersonal relations in another. Shipping has no direct effect on how the story turns out being in the end, because you are on the wrong side of the fantasy/reality divide to exercise directly influence the interpersonal relations.
The most active the typical shipper gets is hoping, arguing their case and maybe giving suggestions to the creative staff that can decide whether the relationship will come to pass or not. Only the last of these could be considered matchmaking in any honest capacity. Well, actually they could also create their own unauthorized addition to the story to play out the fantasy somewhat, and they often do. However, that amounts to playing god with alternate continuity versions of the characters than the ones originally 'shipped.
Showing the Difference
Of course, it's easy just to make an assertion, but it is another thing to prove it.
Helping me to do that is to demonstrate something I may have hinted at in my explanation: The lack of influence is not the only difficulty in using the word matchmaking though. The other factor, is that the matchmaker can be a character archetype for people within the same story.
I think the best demonstration of this is to show how the word matchmaker is used in contexts of literary criticism, and the best example I can think of for that is The Parent Trap.
This is a book, famously adapted into a live action technicolor movie by disney in 1961 by Disney which is about twin daughters who seek to rekindle their parents's love for each other for the sake of reuniting their family. The twins are often and accurately described as matchmakers who do matchmaking:
The Twin Test: A Clean Romance by Rule Sinara
"I've seen The Parent Trap.” On DVD, years ago, at her uncle and aunt's house in Nairobi since there was no TV at Busara. “That movie wasn't about individuality. It was about the twins trying to be matchmakers to get their parents back together,"
Twins in Contemporary Literature and Culture: Look Twice By Juliana De Nooy
And secondly, apart from the occasional comedy of confusion (such as Big Business) and the recurrent 'family entertainment' plot of twin girls matchmaking for their parents (The Parent Trap and its remakes,5 the overwhelming majority of these films are thrillers involving deadly rivalry between good and evil twin sisters.
When people at the bookclub gushes about how Ron Wesley and Herminone Granger from J.K. Rowling's Harry Potter series were always destined to be together, or their peers argue that Harry would have been the better match, that's shipping, as exemplified by the opening line for the Feburary 2nd, 2014 Variety article J.K. Rowling Regrets Pairing Hermione with Ron Instead of Harry Potter by Alex Steadmen
Ron/Hermione shippers, brace yourself: J.K. Rowling thinks the famous pairing was a mistake.
I hope you shall forgive me for not reinforcing this one as much. It is mostly net-slang, and while I could direct you to a variety of discussions where the word is used, such like Final Fantasy Shippers on the Caves of Narshe Forum, it would be difficult for me to source much that is much more authoritative than that, and I also have to tread carefully to avoid hitting disturbingly erotic content that may violate the Code of Conduct.
If you're curious about other uses, you may want to visit some fanfic websites, or maybe not: You see some things may just better left unknown, like how people write about the dysfunctional relationship of Cloud and Sephiroth in the game Final Fantasy VII. Suffice it to say, any place people discuss Japanese pop culture, there will be 'shippers.
A Possible Match
While shipping and matchmaking are both very distinct words, I would suppose that both concepts have considerable overlap with the concept of pairing, which is used in both matchmaking and literary criticism. An example of how the word is used in literary criticism, to establish a an interpersonal character dynamic, can be found in the archive of the May 16th New York Times review Screen: Cruise in Top Gun, by Walter Goodman:
Tom Cruise brings little but a good build to the role of Maverick, and the role of the astrophysicist brings little but impossible lines (''When I first met you, you were larger than life'') to attractive Kelly McGillis. The characters don't pair up well; she's much too classy for him.
While that is not quite exactly the same, the word pairing and shipping are often used in similar contexts. Since we're referencing T.V. Tropes anyway, I might as well share the Crack Pairing:
Shipping beyond all bounds of sanity. There are official couples, there are couples drawn from more-or-less subjective subtext, and there are clearly non-canon pairings that still kind of make sense... and then there are pairings that make you go "What?" Characters who are shipped together despite barely even having a relationship in canon. Sometimes they haven't even met in canon. Sometimes they don't even belong to the same 'verse (that's what Crossovers are for, after all) or to the same species. Sometimes they aren't even both carbon-based lifeforms.
Crack pairings range from the making-you-scratch-your-head-in-puzzlement weird, to the gouging-your-own-eyes-out-with-a-fork weird. But they always leave you asking "Why would anybody think these two belong together?!" [edited emphasis]
The idea there is that you would have to be mentally impaired by drugs in order to support or maybe even think of the 'ship in the first place.
Solution 2:
Was “matchmaking” the equivalent of today's “shipping”?
The simple answer is "No". The terms represent fundamentally different functions, their only connection being that they both reflect one person's desire that two other individuals enter into a relationship that is a step beyond "just friends".
Shipping is a fan-based desire for two people or characters to end up in a romantic relationship. Matchmaking, on the other hand, is an intentional effort to arrange a match, especially "to bring two unmarried individuals together in an attempt to promote a marriage". The two terms are no more synonymous than "wishing" and "doing".
For example, it makes no sense whatsoever to consider matchmaking involving two deceased persons (say, Rock Hudson and Doris Day), but it's perfectly reasonable for a fan of the movie Pillow Talk to ship the characters played by the two actors.
Alternatively, consider Gregory Peck and Audrey Hepburn in Roman Holiday. How many fans must have shipped these two box office favourites, hoping they might replicate their on-screen romance in real life? Obviously they would have used a different term, since that usage of shipping didn't exist in 1953 – but their choice of expression wouldn't have been matchmaking, since it would be nonsensical to think a mere fan could even meet the two superstars, let alone arrange a match between them.
[As a relevant aside, Hepburn actually met her eventual husband (actor Mel Ferrer) at a cocktail party hosted by Peck, but it would too great a stretch to suggest Peck was a matchmaker for the couple.]
Solution 3:
But was there a yesteryear equivalent of “shipping”?
A word or phrase before the 1990s that meant you wanted two people to become romantically involved with one another?
I suspect not, and have found no evidence of one. Most probably – IMHO – because the need for such a term (or, at least, the desire to make a contraction from relationship/worship) only came about once the internet became "a thing".
According to an article from The Atlantic, the concept of fan-fiction and alternative pairings dates back a long time:
Shipping may have achieved prominence in the burgeoning world of Internet fan fiction, but the phenomenon, if not the expression, goes back at least a hundred years, when Sybil Brinton, a wealthy Englishwoman in her forties, wrote the first known work of Jane Austen fan fiction, "Old Friends and New Fancies," in 1913. In this self-proclaimed "sequel," Brinton mimicked Jane Austen's voice as she imagined non-canonical pairings of well-loved characters from all six of Austen’s novels.
Source: 'Shipping' and the Enduring Appeal of Rooting for Love from The Atlantic website.
But notes nothing else until the 1970s and Star Trek giving rise to the modern era of fan-ficton, Kirk-Spock pairings ("K/S") and the more general "slash" fiction.
According to the OED, the earliest citations of shipping and the related shipper are from 1998 (X-Files Official Mag. Winter 8/1) and 1996 (alt.tv.x-files, Usenet newsgroup) respectively. Their citations for related terms are earlier (1944 for "fan fiction", 1984 for "slash" and 1977 for "K/S" (the origin of the term "slash")), but – where they include a term for what is now "shipping" – only use "relationship". For example, the OED's earliest citations for "K/S" are:
1977 Obsc'zine Aug. 5/1: I am not trying to attack a Kirk/Spock sexual relationship in general.
1978 Obsc'zine 20 May 89: She concentrated on the why of the popularity of the K/S relationship stories.